CYCLOSERINE

First approved in 1956

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C3H6N2O2
Molecular Weight	102.0919
Optical Activity	( + )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H]1CONC1=O

InChI

InChIKey=DYDCUQKUCUHJBH-UWTATZPHSA-N

InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C3H6N2O2
Molecular Weight	102.0919
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e1e08327-4b90-463e-bb2a-22438cabcef2
Curator's Comment: description was created based on several sources, including ISBN-13: 978-0199337149

Cycloserine was discovered simultaneously in 1954 by Eli Lilly and Merck. The drug was approved for the treatment of active pulmonary and extrapulmonary tuberculosis and marketed under the name Seromycin (among the others). Cycloserine suppresses the synthesis of bacterial wall by inhibitin two enzymes: alanine racemase and d-alanine ligase.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Alanine racemase 2 Target ID: CHEMBL2031 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4919992	Inhibitor 8504
D-alanylalanine synthetase 1 Target ID: CHEMBL2030 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4919992	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tuberculosis 83 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e1e08327-4b90-463e-bb2a-22438cabcef2	Curative		Approved 8583	SEROMYCIN Approved Use Seromycin is indicated in the treatment of active pulmonary and extrapulmonary tuberculosis (including renal disease) when the causative organisms are susceptible to this drug and when treatment with the primary medications (streptomycin, isoniazid, rifampin, and ethambutol) has proved inadequate. Launch Date 1964

C_max

Value	Dose	Co-administered	Analyte	Population
42.92 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25869627	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		D-CYCLOSERINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
643.29 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25869627	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		D-CYCLOSERINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
13.27 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25869627	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		D-CYCLOSERINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-002615	http://www.3bsc.com/index/pro_info.php?id=24506
AA Blocks	AA00IBP7	http://www.aablocks.com/goods/Goods/detail?id=AA00IBP7
Aaron Chemicals	AR00ICGZ	http://www.aaronchem.com/68-41-7
abcr GmbH	AB115191	http://www.abcr.com/shop/en/AB115191
abcr GmbH	AB402793	http://www.abcr.com/shop/en/AB402793
AbMole Bioscience	M5554	http://www.abmole.com/products/d-cycloserine.html
Acadechem	ACDS-064964	http://www.acadechemical.com/product/139663
Achemtek	0104-016419	http://www.achemtek.com/68-41-7
Acorn PharmaTech	ACN-034126	http://www.acornpharmatech.com/
Acros Organics	AC228480010	https://www.fishersci.com/shop/products/d-cycloserine-98-acros-organics/AC228480010
Acros Organics	AC228480050	https://www.fishersci.com/shop/products/d-cycloserine-98-acros-organics/AC228480050
Acros Organics	AC228480250	https://www.fishersci.com/shop/products/d-cycloserine-98-acros-organics-2/AC228480250
Adooq BioScience	A10291	https://www.adooq.com/d-cycloserine.html
AEchem Scientific Corp., USA	AE1-018090	http://www.aechemsc.com/info_products/AE1-018090.php
AK Scientific, Inc. (AKSCI)	K138	http://www.aksci.com/item_detail.php?cat=K138
Alfa Aesar	A18000	https://www.alfa.com/en/catalog/A18000/
Alfa Chemistry	68-41-7	https://www.alfa-chemistry.com/d-cycloserine-cas-68-41-7-item-293275.htm
Alfa Chemistry	AP68417	https://reagents.alfa-chemistry.com/product/d-cycloserine-cas-68-41-7-15086.html
Alfa Chemistry	AP68417-A	https://reagents.alfa-chemistry.com/product/cycloserine-cas-68-41-7-15087.html
Alichem	471000121	http://www.alichem.com/en/products/68-41-7.html
Angene	AGN-PC-0O93A3	http://www.angenechemical.com/productshow/AGN-PC-0O93A3.html
ApexBio Technology	B1721	http://www.apexbt.com/d-cycloserine-28841.html
AstaTech, Inc.	50854	http://www.astatechinc.com/CPSResult.php?CRNO=2085
Aurora Fine Chemicals LLC	K04.000.876	http://online.aurorafinechemicals.com/info?ID=K04.000.876
Aurum Pharmatech LLC	M-3650	http://www.Aurumpharmatech.com/Product/ProductDetails/M_3650
AvaChem Scientific	6241	https://www.avachem.com/productSearch.asp?6241
BioSynth	C-9390	https://www.biosynth.com/en/products/life-science/culture-media-additives/products/C-9390.html
BioSynth	C-9400	http://www.biosynth.com/index.asp?topic_id=97&g=19&m=249&feld=katno&wert=C-9400
BLD Pharm	BD9333	http://www.bldpharm.com/products/68-41-7.html
Capot Chemical	5763	http://www.capotchem.com/en/5763.htm
Capot Chemical	PubChem5763	http://www.capotchem.com/en/5763.htm
Chem Scene	CS-2395	http://www.chemscene.com/68-41-7.html
Chemenu	CM110202	http://www.chemenu.com/products/CM110202
ChemMol	1030362	http://www.chemmol.com/chemmol/1030362.html
ChemMol	30111597	http://www.chemmol.com/chemmol/30111597.html
ChemMol	44027239	http://www.chemmol.com/chemmol/44027239.html
ChemMol	99122245	http://www.chemmol.com/chemmol/99122245.html
Chemspace	CSSB00000765999	https://chem-space.com/CSSB00000765999
CSNpharm	CSN19477	https://www.csnpharm.com/products/d-cycloserine.html
DC Chemicals	DCAPI1304	http://www.dcchemicals.com//product_show-D_Cycloserine.html
Enamine	Z1522567171	https://www.enaminestore.com/catalog/Z1522567171
eNovation Chemicals	D492514	https://www.enovationchem.com/ProductDetails.asp?ProductID=D492514
eNovation Chemicals	D682049	https://www.enovationchem.com/ProductDetails.asp?ProductID=D682049
eNovation Chemicals	D910419	https://www.enovationchem.com/ProductDetails.asp?ProductID=D910419
eNovation Chemicals	Y1050283	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1050283
Glentham Life Sciences	GA9717	http://www.glentham.com/products/product/GA9717/
Hello Bio	HB0234	http://www.hellobio.com/dcycloserine.html
iChemical	EBD2198208	http://www.ichemical.com/products/68-41-7.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00173123	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00173123
LGC Standards	DRE-C11836200	https://www.lgcstandards.com/US/en/p/DRE-C11836200
LGC Standards	LGCFOR3028.00	https://www.lgcstandards.com/US/en/p/LGCFOR3028.00
LGC Standards	MM3028.00	https://www.lgcstandards.com/US/en/p/MM3028.00
Matrix Scientific	72929	https://www.matrixscientific.com/072929.html
mcule	MCULE-4212827696	https://mcule.com/MCULE-4212827696/
MedChem Express	HY-B0030	https://www.medchemexpress.com/D-Cycloserine.html
OChem	2077	http://www.ocheminc.com/index.php?act=psearch&pid=005C353
Parchem	117245	https://www.parchem.com/chemical-supplier-distributor/4-Aminoisoxazolidin-3-one-117245.aspx
Renno Tech	RL04615	http://www.rennotech.com/product_show.asp?id=4864
Shanghai Send Pharmaceutical Technology Co., Ltd	send32482	http://shsendpharm.com/
Sigma-Aldrich	1158005_USP	https://www.sigmaaldrich.com/catalog/product/usp/1158005?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	30020_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/30020?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	C3909_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/c3909?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	C6880_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/c6880?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	PHR1765_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/phr1765?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S049307	http://www.sinfoobiotech.com/product/1052705
Smolecule	S524744	http://www.smolecule.com/products/s524744
Smolecule	S793365	https://www.smolecule.com/products/s793365
TCI (Tokyo Chemical Industry)	C1189	http://www.tcichemicals.com/eshop/en/us/commodity/C1189/index.html
THE BioTek	bt-266218	https://www.thebiotek.com/product/inhibitors/bt-266218
VladaChem	VL141602	https://www.vladachem.com/product.php?products=68-41-7
VladaChem	VL263773-1G	https://www.vladachem.com/product.php?products=68-41-7
Watanabe Chemical Ind.	H00231	https://www.watanabechem.co.jp/en/search/details.php?code=H00231
Yuhao Chemical	LT4743	http://www.chemyuhao.com/68-41-7.html

PubMed

Title	Date	PubMed
A six-month, placebo-controlled trial of D-cycloserine co-administered with conventional antipsychotics in schizophrenia patients.	2005-04	15502972
Effects of D-cycloserine on negative symptoms in schizophrenia.	2004-12-01	15474895
Cognitive enhancers as adjuncts to psychotherapy: use of D-cycloserine in phobic individuals to facilitate extinction of fear.	2004-11	15520361
A pilot study of D-cycloserine in subjects with autistic disorder.	2004-11	15514414
Structural evidence that alanine racemase from a D-cycloserine-producing microorganism exhibits resistance to its own product.	2004-10-29	15302886
Self-protection mechanism in D-cycloserine-producing Streptomyces lavendulae. Gene cloning, characterization, and kinetics of its alanine racemase and D-alanyl-D-alanine ligase, which are target enzymes of D-cycloserine.	2004-10-29	15302885
Facilitation of fear extinction by D-cycloserine: theoretical and clinical implications.	2004-10-07	15466301
Multidrug resistant miliary tuberculosis and Pott's disease in an immunocompetent patient.	2004-10	15494824
Cell-surface alterations in class IIa bacteriocin-resistant Listeria monocytogenes strains.	2004-09	15347760
Differential neuroprotective effects of the NMDA receptor-associated glycine site partial agonists 1-aminocyclopropanecarboxylic acid (ACPC) and D-cycloserine in lithium-pilocarpine status epilepticus.	2004-09	15288514
Pharmacy data for tuberculosis surveillance and assessment of patient management.	2004-08	15496244
Pharmacotherapy for performance anxiety disorders: occasionally useful but typically contraindicated.	2004-08	15241814
Consolidation of human motor cortical neuroplasticity by D-cycloserine.	2004-08	15199378
Responsiveness to brightness change in male and female rats following treatment with the partial agonist of the N-methyl-D-aspartate receptor, D-cycloserine.	2004-07-09	15196787
Treatment and follow-up of HIV-negative multidrug-resistant tuberculosis patients in an infectious diseases reference hospital, Buenos Aires, Argentina.	2004-06	15182150
Surveillance of Mycobacterium tuberculosis susceptibility to second-line drugs in Hong Kong, 1995-2002, after the implementation of DOTS-plus.	2004-06	15182147
Psychiatric issues in the management of patients with multidrug-resistant tuberculosis.	2004-06	15182146
D-cycloserine and the facilitation of extinction of conditioned fear: consequences for reinstatement.	2004-06	15174928
Ceramide synthesis correlates with the posttranscriptional regulation of the sterol-regulatory element-binding protein.	2004-05	15132973
Glycine and D-cycloserine attenuate vacuous chewing movements in a rat model of tardive dyskinesia.	2004-04-09	15033429
Six-month therapy with aerosolized interferon-gamma for refractory multidrug-resistant pulmonary tuberculosis.	2004-04	15082886
Surprises and omissions in toxicology.	2004-03	15141993
Self-administered, standardized regimens for multidrug-resistant tuberculosis in South Korea.	2004-03	15139476
Effects of NMDA receptor-related agonists on learning and memory impairment in olfactory bulbectomized mice.	2004-03	15071606
Model structures of the N-methyl-D-aspartate receptor subunit NR1 explain the molecular recognition of agonist and antagonist ligands.	2004-03	14960371
Reactions of serine palmitoyltransferase with serine and molecular mechanisms of the actions of serine derivatives as inhibitors.	2004-02-03	14744154
Comparative effects of glycine and D-cycloserine on persistent negative symptoms in schizophrenia: a retrospective analysis.	2004-02-01	15061240
A microplate indicator-based method for determining the susceptibility of multidrug-resistant Mycobacterium tuberculosis to antimicrobial agents.	2004-02	15139456
New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method.	2004-01	14645324
Pharmacokinetics and relative bioavailability of clofazimine in relation to food, orange juice and antacid.	2004	15525560
Pharmacological treatments of cerebellar ataxia.	2004	15233578
Cycloserine and threo-dihydrosphingosine inhibit TNF-alpha-induced cytotoxicity: evidence for the importance of de novo ceramide synthesis in TNF-alpha signaling.	2003-12-07	14654222
In vitro activity of C-8-methoxy fluoroquinolones against mycobacteria when combined with anti-tuberculosis agents.	2003-12	14613961
Society for Neuroscience meeting. Pills and games help conquer fear.	2003-11-21	14631016
D-cycloserine facilitates synaptic plasticity but impairs glutamatergic neurotransmission in rat hippocampal slices.	2003-11	14530208
Comparative roles of levofloxacin and ofloxacin in the treatment of multidrug-resistant tuberculosis: preliminary results of a retrospective study from Hong Kong.	2003-10	14555582
Genome-wide transcriptional profiling of the response of Staphylococcus aureus to cell-wall-active antibiotics reveals a cell-wall-stress stimulon.	2003-10	14523105
Molecular cloning of a D-cycloserine resistance gene from D-cycloserine-producing Streptomyces garyphalus.	2003-09	14632285
Substrate reduction intervention by L-cycloserine in twitcher mice (globoid cell leukodystrophy) on a B6;CAST/Ei background.	2003-08-14	12865135
Multidrug-resistant tuberculosis in HIV-negative patients, Buenos Aires, Argentina.	2003-08	12967495
D-cycloserine-Naloxone interactions in opioid-dependent humans under a novel-response naloxone discrimination procedure.	2003-08	12940503
Effects of antibiotics that inhibit the bacterial peptidoglycan synthesis pathway on moss chloroplast division.	2003-07	12881507
D-cycloserine for the treatment of ataxia in spinocerebellar degeneration.	2003-06-15	12736088
A side reaction of alanine racemase: transamination of cycloserine.	2003-05-20	12741835
Subunit interaction of monomeric alanine racemases from four Shigella species in catalytic reaction.	2003-04-25	12725937
Effects of D-cycloserine on extinction of conditioned freezing.	2003-04	12708530
N(2)-substituted D,L-cycloserine derivatives: synthesis and evaluation as alanine racemase inhibitors.	2003-02	12715876
[Incidence of adverse reactions to chemotherapy and their types in adolescents with tuberculosis].	2003	12652980
Spectrum of drugs against atypical mycobacteria: how valid is the current practice of drug susceptibility testing and the choice of drugs?	1992-12	1303690
Cycloserine: antituberculous activity in vitro and in the experimental animal.	1956-04	13302684

Patents

Sample Use Guides

In Vivo Use Guide

The usual dosage is 500 mg to 1 g daily in divided doses monitored by blood levels. The initial adult dosage most frequently given is 250 mg twice daily at 12–hour intervals for the first 2 weeks. A daily dosage of 1 g should not be exceeded.

Route of Administration: Oral

In Vitro Use Guide

Multidrug resistant Mycobacterium tuberculosis isolates were incubated with 20 uL of cycloserine. 5 different cycloserine concentrations (8, 16, 32, 64, and > 64 ug/mL).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:50:14 GMT 2025` Edited by `admin` on `Mon Mar 31 17:50:14 GMT 2025`
Record UNII	95IK5KI84Z
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CYCLOSERINE

Official Name

English

D-CYCLOSERINE

Preferred Name

English

(+)-4-AMINO-3-ISOXAZOLIDINONE

Systematic Name

English

CYCLOSERINE [WHO-IP]

Common Name

English

SEROMYCIN

Brand Name

English

CYCLOSERINE [USP MONOGRAPH]

Common Name

English

CYCLOSERINE [MI]

Common Name

English

CYCLOSERINUM [WHO-IP LATIN]

Common Name

English

ORIENTOMYCIN

Common Name

English

3-ISOXAZOLIDINONE, 4-AMINO-, (R)-

Systematic Name

English

CYCLOSERINE [USP IMPURITY]

Common Name

English

NSC-76029

Code

English

CYCLOSERINE [ORANGE BOOK]

Common Name

English

cycloserine [INN]

Common Name

English

CYCLOSERINE [VANDF]

Common Name

English

Cycloserine [WHO-DD]

Common Name

English

NSC-154851

Code

English

CYCLOSERINE [JAN]

Common Name

English

CYCLOSERINE [HSDB]

Common Name

English

CYCLOSERINE [MART.]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ04AB01