Cyclosporine

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C62H111N11O12
Molecular Weight	1202.6136
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C(=O)[C@H](CC)NC1=O)C(C)C

InChI

InChIKey=PMATZTZNYRCHOR-CGLBZJNRSA-N

InChI=1S/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(39(13)14)62(85)73(51)24/h25,27,34-47,49-52,75H,26,28-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b27-25+/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50+,51+,52-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C62H111N11O12
Molecular Weight	1202.6136
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 12
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24341787 | http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050573s041,050574s051,050625s055lbl.pdf | http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050715s035,050716s038lbl.pdf | http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050790s024s025lbl.pdf

Cyclosporins are cyclic polypeptide macrolides that were originally derived from the soil fungus Tolypocladium inflatum. Cyclosporine (also known as cyclosporine A) was discovered by Sandoz and developed for the tretment of immune disorders. The drug was approved by FDA for such diseases as Rheumatoid Arthritis, Psoriasis (Neoral), Keratoconjunctivitis sicca (Restasis) and prevention of transplant rejections (Neoral and Sandimmune). Cyclosporine’s primary immunosuppressive mechanism of action is inhibition of T-lymphocyte function. Upon administration cyclosporine binds to cyclophilin A and thus inhibits calcineurin, leading to immune system suppression.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclophilin A 1 Target ID: CHEMBL1949 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24341787	Binding Agent 1076		36.8 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Keratoconjunctivitis sicca 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050790s024s025lbl.pdf	Palliative	Approved 8583	RESTASIS Approved Use Restasis is a calcineurin inhibitor immunosuppressant indicated to increase tear production in patients whose tear production is presumed to be suppressed due to ocular inflammation associated with keratoconjunctivitis sicca. Increased tear production was not seen in patients currently taking topical anti-inflammatory drugs or using punctal plugs. Launch Date 2003
Organ rejection in kidney, liver, and heart allogeneic transplants 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050573s041,050574s051,050625s055lbl.pdf	Preventing	Approved 8583	SANDIMMUNE Approved Use Sandimmune (cyclosporine) is indicated for the prophylaxis of organ rejection in kidney, liver, and heart allogeneic transplants. It is always to be used with adrenal corticosteroids. The drug may also be used in the treatment of chronic rejection in patients previously treated with other immunosuppressive agents. Launch Date 1983
Rheumatoid arthritis 320 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050715s035,050716s038lbl.pdf	Primary	Approved 8583	NEORAL Approved Use Neoral is indicated for the treatment of patients with severe active, rheumatoid arthritis where the disease has not adequately responded to methotrexate. Neoral can be used in combination with methotrexate in rheumatoid arthritis patients who do not respond adequately to methotrexate alone. Launch Date 1995
Psoriasis 87 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050715s035,050716s038lbl.pdf	Primary	Approved 8583	NEORAL Approved Use Neoral is indicated for the treatment of adult, nonimmunocompromised patients with severe (i.e., extensive and/or disabling), recalcitrant, plaque psoriasis who have failed to respond to at least one systemic therapy (e.g., PUVA, retinoids, or methotrexate) or in patients for whom other systemic therapies are contraindicated, or cannot be tolerated. Launch Date 1995

C_max

Value	Dose	Co-administered	Analyte	Population
1220 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12118899	5.26 mg/kg single, oral dose: 5.26 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		CYCLOSPORINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
3301 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12118899	5.26 mg/kg single, oral dose: 5.26 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		CYCLOSPORINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
6 h REVIEW https://www.ncbi.nlm.nih.gov/pubmed/3322675	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		CYCLOSPORINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
4 mg/kg 1 times / day multiple, intravenous Dose: 4 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 4 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11313301	unhealthy, 36.7 years (range: 20–67 years) Health Status: unhealthy Age Group: 36.7 years (range: 20–67 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/11313301	Other AEs: Hypertension, Superficial thrombophlebitis... Other AEs: Hypertension (1 patient) Superficial thrombophlebitis (1 patient) Headache (2 patients) Vomiting (1 patient) Hypokalemia (4 patients) Hypomagnesemia (2 patients) Myalgia (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/11313301
0.09 % 2 times / day multiple, ophthalmic Recommended Dose: 0.09 %, 2 times / day Route: ophthalmic Route: multiple Dose: 0.09 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210913Orig1s000MedR.pdf	unhealthy, 61.9 years (range: 23-91 years) Health Status: unhealthy Age Group: 61.9 years (range: 23-91 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210913Orig1s000MedR.pdf	Disc. AE: Musculoskeletal disorder, Connective tissue disorders... Other AEs: Throat irritation... AEs leading to discontinuation/dose reduction: Musculoskeletal disorder (moderate, 1 patient) Connective tissue disorders (moderate, 1 patient) General system disorders NEC (grade 1-2, 11 patient) Instillation site pain (mild, 11 patient) Instillation site pruritus (mild, 1 patient) Candida infection (moderate, 1 patient) Macular fibrosis (mild, 1 patient) Sinusitis (mild, 1 patient) Vision blurred (mild, 1 patient) Eye irritation (mild, 1 patient) Conjunctival hyperemia (moderate, 1 patient) Foreign body sensation in eyes (severe, 1 patient) Headache (grade 1-2, 2 patients) Eye pain (mild, 2 patients) Other AEs: Throat irritation (mild, 1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210913Orig1s000MedR.pdf
10 g single, oral Highest studied dose Dose: 10 g Route: oral Route: single Dose: 10 g Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050573s041,050574s051,050625s055lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050573s041,050574s051,050625s055lbl.pdf	Other AEs: Vomiting, Drowsiness... Other AEs: Vomiting Drowsiness Headache Tachycardia Impaired renal function (grade 2) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050573s041,050574s051,050625s055lbl.pdf
3 mg/kg 1 times / day steady, oral Dose: 3 mg/kg, 1 times / day Route: oral Route: steady Dose: 3 mg/kg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00974142	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT00974142	Other AEs: Renal insufficiency, Gastrointestinal upset... Other AEs: Renal insufficiency (below serious, 4 patients) Gastrointestinal upset (below serious, 4 patients) Hyperkalemia (below serious, 2 patients) Hypertension (below serious, 1 patient) Tremor (below serious, 1 patient) Cramp muscle (below serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT00974142
5 mg/kg 2 times / week steady, oral Dose: 5 mg/kg, 2 times / week Route: oral Route: steady Dose: 5 mg/kg, 2 times / week Sources: https://clinicaltrials.gov/ct2/show/NCT00438360	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT00438360	Other AEs: Breast mass, Abdominal pain upper... Other AEs: Breast mass (serious, 1 patient) Abdominal pain upper (below serious, 12 patients) Hypertriglyceridaemia (below serious, 8 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00438360

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A1 246 UGT1A4 98 UGT1A6 136 UGT2B7 197 UGT2B10 31 OATP1B1 1079 OATP1B3 961 NTCP 39 BCRP 910 OATP2 4 MDR 1	UGT1A1 479 UGT1A3 470 UGT1A4 399 UGT1A6 343 UGT1A7 249 UGT1A8 323 UGT1A9 423 UGT1A10 331 UGT2B4 278 UGT2B7 456 UGT2B15 236 P-gp 2052	CYP1A1 151 CYP1A2 832 CYP2D1 2

Drug as perpetrator

Target	Modality	Activity
UGT1A6 171	inhibitor 4027 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	no
UGT2B10 33	inhibitor 4027 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	no
UGT2B7 210	inhibitor 4027 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	no
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23881596/ Page: -	yes [IC50 0.05 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23881596/ Page: -	yes [IC50 0.1 uM]
OATP2 4	inhibitor 4027 Sources: https://jpet.aspetjournals.org/content/304/2/610.short Page: -	yes [IC50 0.2 uM]
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23881596/ Page: -	yes [IC50 2 uM]
UGT1A4 100	inhibitor 4027 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	yes [IC50 23 uM]
NTCP 40	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23881596/ Page: -	yes [IC50 4.5 uM]
UGT1A1 303	inhibitor 4027 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	yes [IC50 48 uM]
CYP1A1 272	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/8361996/ Page: -	yes
CYP1A2 2333	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/8361996/ Page: -	yes
CYP2D1 8	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/8361996/ Page: -	yes
MDR 1	inhibitor 4027 Sources: http://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.915.5144&rep=rep1&type=pdf Page: -	yes

Drug as victim

Target	Modality	Activity
UGT2B7 456	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	major
UGT1A1 479	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	minor
UGT1A10 331	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	minor
UGT1A3 470	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	minor
UGT1A4 399	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT1A6 343	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT1A7 249	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT1A8 323	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT1A9 423	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT2B15 236	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT2B4 278	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
CYP3A4 1946	substrate 4014 Sources: https://link.springer.com/article/10.1007%2FBF03190040 Page: -	yes
P-gp 2052	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S0085253815520577 Page: -	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/22128262/ Page: -

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0266	http://www.3bsc.com/index/pro_info.php?id=19622
AA Blocks	AA005L8Q	https://www.aablocks.com/goods/Goods/detail?id=AA005L8Q
Aaron Chemicals	AR005M0I	http://www.aaronchem.com/79217-60-0
abcr GmbH	AB181158	http://www.abcr.de/shop/en/AB181158
AbMole Bioscience	M1831	http://www.abmole.com/products/cyclosporine-a.html
AbMole Bioscience	M5541	http://www.abmole.com/products/cyclosporine.html
Achemtek	0104-013119	http://www.achemtek.com/59865-13-3
Acorn PharmaTech	ACN-029253	http://www.acornpharmatech.com/
Adooq BioScience	A10260	https://www.adooq.com/cyclosporin-a.html
AHH Chemical co.,ltd	API-1252	http://www.ahhchemical.com/product/API-1252.html
AHH Chemical co.,ltd	MT-01094	http://www.ahhchemical.com/product/MT-01094.html
AK Scientific, Inc. (AKSCI)	J10181	http://www.aksci.com/item_detail.php?cat=J10181
AK Scientific, Inc. (AKSCI)	J90049	http://www.aksci.com/item_detail.php?cat=J90049
AK Scientific, Inc. (AKSCI)	Q333	http://www.aksci.com/item_detail.php?cat=Q333
Alfa Chemistry	AP59865133-A	https://reagents.alfa-chemistry.com/product/cyclosporin-a-ready-made-solution-cas-59865-13-3-13790.html
Alfa Chemistry	AP59865133-B	https://reagents.alfa-chemistry.com/product/cyclosporine-cas-59865-13-3-13791.html
Alfa Chemistry	AP59865133-C	https://reagents.alfa-chemistry.com/product/cyclosporin-a-cas-59865-13-3-13792.html
Alfa Chemistry	AP59865133-D	https://reagents.alfa-chemistry.com/product/cyclosporin-a-solution-cas-59865-13-3-13793.html
Alfa Chemistry	AP59865133-E	https://reagents.alfa-chemistry.com/product/cyclosporin-a-solution-cas-59865-13-3-13794.html
Alsachim	950	http://www.alsachim.com/product-C2629-glo.bal-view.html
Ambinter	Amb1865584	http://www.ambinter.com/reference/1865584
ApexBio Technology	A5938	http://www.apexbt.com/cyclosporine.html
ApexBio Technology	B1922	http://www.apexbt.com/cyclosporin-a.html
Aurora Fine Chemicals LLC	A13.105.543	http://online.aurorafinechemicals.com/info?ID=A13.105.543
AvaChem Scientific	1968	http://www.avachem.com/productSearch.asp?1968
Avantor Inc	101096-750	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101096-750
BioCrick	BCC2559	http://www.biocrick.com/Cyclosporine-BCC2559.html
BioCrick	BCC4773	http://www.biocrick.com/Cyclosporin-A-BCC4773.html
Biopurify Phytochemicals	BP0438	http://www.phytopurify.com/CyclosporinA-p-4184.html
BioSynth	Q-200913	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/Q-200913.html
BOC Sciences	59865-13-3	https://www.bocsci.com/cyclosporine-cas-59865-13-3-item-84-300196.html
Calbiochem	239835	http://www.emdbiosciences.com/product/239835
Chem Scene	CS-2761	http://www.chemscene.com/59865-13-3.html
Chemenu	CM119904	http://www.chemenu.com/products/CM119904
ChemMol	2101379	http://www.chemmol.com/chemmol/2101379.html
ChemMol	49422981	http://www.chemmol.com/chemmol/49422981.html
Chemspace	CSSB00161189749	https://chem-space.com/CSSB00161189749
Chemspace	CSSB02125554483	https://chem-space.com/CSSB02125554483
Chemspace	CSSS02125561432	https://chem-space.com/CSSS02125561432
Clearsynth	CS-O-06250	https://www.clearsynth.com/en/CSO06250.html
DC Chemicals	DC4115	http://www.dcchemicals.com/product_show-Cyclosporin_A.html
EMD Millipore	239835	http://www.emdbiosciences.com/product/239835
eNovation Chemicals	D386493	http://www.enovationchem.com/productDetails.asp?productID=D386493
Excenen	EX-A4110	https://www.excenen.com/searchresultlist.php?id=EX-A4110
Glentham Life Sciences	GA6323	http://www.glentham.com/products/product/GA6323/
Hairui	HR132082	http://www.hairuichem.com/en/product/59865-13-3.html
Huateng Pharma	F80017934	http://en.huatengsci.com/product/Cyclosporin-A.html
iChemical	EBD2126862	http://www.ichemical.com/products/59865-13-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
iChemical	EBD2224706	http://www.ichemical.com/products/79217-60-0.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN01327074	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01327074
LGC Standards	DRE-C11836300	https://www.lgcstandards.com/US/en/p/DRE-C11836300
LGC Standards	MM0241.00	https://www.lgcstandards.com/US/en/p/MM0241.00
MedChem Express	HY-B0579	https://www.medchemexpress.com/cyclosporin-a.html
MolPort	MolPort-000-760-988	https://www.molport.com/shop/molecule-link/MolPort-000-760-988
MolPort	MolPort-005-934-008	https://www.molport.com/shop/molecule-link/MolPort-005-934-008
MolPort	MolPort-006-705-994	https://www.molport.com/shop/molecule-link/MolPort-006-705-994
MolPort	MolPort-023-220-498	https://www.molport.com/shop/molecule-link/MolPort-023-220-498
OChem	2004	http://www.ocheminc.com/index.php?act=psearch&pid=865C133
Octagon Chemicals	API Cyclosporine 59865-13-3	https://octagonchem.com/products/apis/cyclosporine/
Parchem	10883	http://www.parchem.com/chemical-supplier-distributor/Cyclosporin-000883.aspx
Selleck Chemicals	S1514	http://www.selleckchem.com/products/Cyclosporine.html
Sigma-Aldrich	1158504_USP	https://www.sigmaaldrich.com/catalog/product/usp/1158504?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	30024_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/30024?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	32425_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/32425?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	C1832_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/c1832?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	C2163000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/c2163000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S061040	http://www.sinfoobiotech.com/product/1064443
TCI (Tokyo Chemical Industry)	C2408	http://www.tcichemicals.com/eshop/en/us/commodity/C2408/index.html
THE BioTek	bt-242573	https://www.thebiotek.com/product/peptides/bt-242573
Tocris	1101	https://www.tocris.com/products/cyclosporin-a_1101
TOKU-E Company	C042	http://www.toku-e.com/product/cyclosporin_a/
Vitas-M Laboratory	STK177328	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=STK177328&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
VladaChem	VL265833-1G	https://www.vladachem.com/product.php?products=59865-13-3
Wuhan Atomole Chemicals Co., Ltd.	AT-12519	http://www.atomole.com/en/products-view.asp?id=2269

PubMed

Title	Date	PubMed
Myelodysplastic syndrome complicated by autoimmune hemolytic anemia: remission of refractory anemia following mycophenolate mofetil.	2002-12	12483369
Sirolimus: new preparation. No tangible advance in renal transplantation.	2002-12	12469693
Expression of TGF-beta and fibrogenic genes in transplant recipients with tacrolimus and cyclosporine nephrotoxicity.	2002-12	12427154
Sirolimus (Rapamune) in renal transplantation.	2002-11	12394605
Evaluation of carcinogenic responses in the Eker rat following short-term exposure to selected nephrotoxins and carcinogens.	2002-10-10	12371664
Dissociated ROS production and ceramide generation in sulfasalazine-induced cell death in Raw 264.7 cells.	2002-10	12377949
Oxidative stress in kidney transplant patients with calcineurin inhibitor-induced hypertension: effect of ramipril.	2002-10	12352326
Pimecrolimus inhibits up-regulation of OX40 and synthesis of inflammatory cytokines upon secondary T cell activation by allogeneic dendritic cells.	2002-10	12296857
Interaction of cytochrome P450 3A inhibitors with P-glycoprotein.	2002-10	12235267
Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line.	2002-09-01	12387747
Long-term comparison of tacrolimus- and cyclosporine-induced nephrotoxicity in pediatric heart-transplant recipients.	2002-09	12243498
Dermatomyositis associated with membranous nephropathy in a 43-year-old female.	2002-08-10	12169874
Oxidative stress and TGFbeta in kidney-transplanted patients with cyclosporin-induced hypertension. Effect of carvedilol and nifedipine.	2002-08	12227681
Angiotensin II regulation of vascular endothelial growth factor and receptors Flt-1 and KDR/Flk-1 in cyclosporine nephrotoxicity.	2002-08	12110003
Calcineurin inhibitors, cyclosporin A and tacrolimus inhibit expression of inducible nitric oxide synthase in colon epithelial and macrophage cell lines.	2002-07-19	12144947
Cyclosporine-associated facial paralysis in a child with renal transplant.	2002-07	12172772
Colchicine myoneuropathy in a renal transplant patient.	2002-07	12122515
Studies of renal injury IV: The GLUT1 gene protects renal cells from cyclosporine A toxicity.	2002-07	12081571
Itraconazole-induced rhabdomyolysis and acute renal failure in a heart transplant recipient treated with simvastatin and cyclosporine.	2002-06-27	12131698
Nephrotoxicity of cyclosporine A and amphotericin B-deoxycholate as continuous infusion in allogenic stem cell transplantation.	2002-06-15	12362282
Enhancement by cyclosporin A of taxol-induced apoptosis of human urinary bladder cancer cells.	2002-05	12086014
Alterations induced by cyclosporine A in myocardial fibers and extracellular matrix in rat.	2002	12168785
End-stage renal disease (ESRD) after orthotopic liver transplantation (OLTX) using calcineurin-based immunotherapy: risk of development and treatment.	2001-12-27	11773892
Severe neurotoxicity of tacrolimus (FK506) after renal transplantation: two case reports.	2001-12-26	11750573
Bone marrow aplasia after pipobroman: an immune-mediated mechanism?	2001-12	11736962
Cyclosporin-induced hypertension.	2001-12	11725176
[Arterial hypertension and oxidative stress induced by cyclosporin. Effect of carvedilol].	2001-11-02	11688356
Fatal acute hepatic failure induced by danazol in a patient with endometriosis and aplastic anemia.	2001-11	11757752
Targeting keratinocyte apoptosis in the treatment of atopic dermatitis and allergic contact dermatitis.	2001-11	11692113
Buerger's disease in a patient with minimal-change nephrotic syndrome.	2001-11	11598405
Vascular endothelial function in cyclosporine and tacrolimus treated renal transplant recipients.	2001-10-27	11685108
Cyclosporine A-induced mammary hyperplasia and hyperprolactinemia in New Zealand White rabbits.	2001-10	11924803
Doxorubicin ototoxicity is induced in mice by combination treatment with cyclosporin A.	2001-10	11718240
Cyclosporin A-induced encephalopathy after allogeneic bone marrow transplantation with prevention of graft-versus-host disease by tacrolimus.	2001-10	11704797
Use of rapamycin in a transplant patient who developed cyclosporin neurotoxicity.	2001-10	11605780
Sirolimus and mycophenolate mofetil for calcineurin-free immunosuppression in renal transplant recipients.	2001-10	11583940
Changes in lipid metabolism and effect of simvastatin in renal transplant recipients induced by cyclosporine or tacrolimus.	2001-10	11583721
Correlates of acute renal failure in patients receiving parenteral amphotericin B.	2001-10	11576359
Silencer activity of NFATc2 in the interleukin-12 receptor beta 2 proximal promoter in human T helper cells.	2001-09-14	11438525
Calcineurin-GATA4 pathway is involved in beta-adrenergic agonist-responsive endothelin-1 transcription in cardiac myocytes.	2001-09-14	11435416
Drug-associated thrombotic thrombocytopenic purpura-hemolytic uremic syndrome.	2001-09	11604563
Cholestasis and regulation of genes related to drug metabolism and biliary transport in rat liver following treatment with cyclosporine A and sirolimus (Rapamycin).	2001-09	11589784
Role of calcineurin in insulin-like growth factor-1-induced hypertrophy of cultured adult rat ventricular myocytes.	2001-09	11548882
Calcineurin-inhibitor related nephrotoxicity- reversibility in paediatric liver transplant recipients.	2001-08-27	11544444
Renal cholesterol accumulation: a durable response after acute and subacute renal insults.	2001-08	11485932
What is proper treatment for Wegener granulomatosis?	2001-07-23	11485512
Functional characterization of the human multidrug transporter, ABCG2, expressed in insect cells.	2001-07-06	11437380
Cyclosporin A for the treatment of patients with chronic idiopathic thrombocytopenic purpura refractory to corticosteroids or splenectomy.	2001-07	11472356
Mycophenolate mofetil monotherapy in liver transplantation.	2001-02-24	11558493
Replacement of calcineurin inhibitors with mycophenolate mofetil in liver-transplant patients with renal dysfunction: a randomised controlled study.	2001-02-24	11558484

Patents

Sample Use Guides

In Vivo Use Guide

Organs transplantation: the initial oral dose of cyclosporine (Sandimmune) should be given 4 to 12 hours prior to transplantation as a single dose of 15 mg/kg. Rheumatoid Arthritis, Psoriasis: the initial dose of cyclosporine (Neoral) is 2.5 mg/kg/day, taken twice daily as a divided (BID) oral dose. Keratoconjunctivitis sicca: instill one drom twice a day in each eye, approximately 12 hours apart.

Route of Administration: Other

In Vitro Use Guide

Human CD4+CD25+ cells isolated from healthy donors were cultured in the presence of 40 or 400 ng/mL of cyclosporine. The suppressive activity of Treg was assessed in mixed leukocyte reactions (MLR) using CD25+ and autologous activated peripheral blood mononuclear cells (PBMC). The drug inhibited the proliferative capacity of PBMC and CD4+CD25+ Treg in a dose-dependent manner.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:11:17 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:17 GMT 2025`
Record UNII	83HN0GTJ6D
Record Status	`FAILED`
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Name

Type

Language

Cyclosporine

Official Name

English

CICLOSPORIN

Preferred Name

English

CYCLOSPORIN A [MI]

Common Name

English

CICLOSPORINUM [WHO-IP LATIN]

Common Name

English

EQUORAL

Common Name

English

CYCLOSPORIN

Common Name

English

CYCLOSPORINE [GREEN BOOK]

Common Name

English

CICLOSPORIN A

Common Name

English

CICLOSPORIN [EP MONOGRAPH]

Common Name

English

GENGRAF

Brand Name

English

RAMIHYPHIN A

Common Name

English

(R-(R*,R*-(E)))-CYCLIC(L-ALANYL-D-ALANYL-N-METHYL-L-LEUCYL-N-METHYL-L-LEUCYL-N-METHYL-L-VALYL-3-HYDROXY-N,4-DIMETHYL-L-2-AMINO-6-OCTENOYL-L-.ALPHA.-AMINOBUTYRYL-N-METHYLGLYCYL-N-METHYL-L-LEUCYL-L-VALYL-N-METHYL-L-LEUCYL)

Common Name

English

NSC-290193

Code

English

NEOPLANTA

Common Name

English

SANDIMMUNE

Brand Name

English

NEORAL

Brand Name

English

SDZ-OXL-400

Code

English

MITOGARD

Brand Name

English

VEVYE

Brand Name

English

OL-27-400

Code

English

NEUROSTAT

Brand Name

English

CYCLOSPORINE [USP-RS]

Common Name

English

ATOPICA

Brand Name

English

CYCLOSPORINE [HSDB]

Common Name

English

OPTIMMUNE

Brand Name

English

CYCLO(((E)-(2S,3R,4R)-3-HYDROXY-4-METHYL-2-(METHYLAMINO)-6-OCTENOYL)-L-2-AMINOBUTYRYL-N-METHYLGLYCYL-N-METHYL-L-LEUCYL-L-VALYL-N-METHYL-L-LEUCYL-L-ALANYL-D-ALANYL-N-METHYL-L-LEUCYL-N-METHYL-L-LEUCYL-N-METHYL-L-VALYL)

Common Name

English

CYCLOSPORINE MICROEMULSION

Common Name

English

VERKAZIA

Brand Name

English

IKERVIS

Brand Name

English

CYCLOSPORINE [IARC]

Common Name

English

CYCLOSPORINE, MODIFIED

Common Name

English

CYCLOSPORINE [VANDF]

Common Name

English

ANTIBIOTIC S-7481F1

Code

English

CICLOSPORIN [JAN]

Common Name

English

CYCLOSPORINE [USAN]

Common Name

English

ciclosporin [INN]

Common Name

English

CYCLOSPORINE [USP IMPURITY]

Common Name

English

CYCLOSPORINE [USP MONOGRAPH]

Common Name

English

CYCLOSPORIN A

Common Name

English

SANG-35

Code

English

27-400

Code

English

CEQUA

Brand Name

English

CYCLOSPORINE [ORANGE BOOK]

Common Name

English

Ciclosporin [WHO-DD]

Common Name

English

CYCLOSPORINE A

Common Name

English

CICLOSPORIN [WHO-IP]

Common Name

English

RESTASIS

Brand Name

English

ZINOGRAF ME

Common Name

English

SANDIMMUN

Brand Name

English

CICLOSPORIN [MART.]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QS01XA18