CEPHALORIDINE

First approved in 1968

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H17N3O4S2
Molecular Weight	415.486
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-]C(=O)C1=C(C[N+]2=CC=CC=C2)CS[C@@H]3[C@H](NC(=O)CC4=CC=CS4)C(=O)N13

InChI

InChIKey=CZTQZXZIADLWOZ-CRAIPNDOSA-N

InChI=1S/C19H17N3O4S2/c23-14(9-13-5-4-8-27-13)20-15-17(24)22-16(19(25)26)12(11-28-18(15)22)10-21-6-2-1-3-7-21/h1-8,15,18H,9-11H2,(H-,20,23,25,26)/t15-,18-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C19H17N3O4S2
Molecular Weight	415.486
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.druginfosys.com/Drug.aspx?drugCode=149&drugName=Cephaloridine&type=6
Curator's Comment: Description was created based on several sources. including http://www.drugbank.ca/drugs/DB09008 and http://onlinelibrary.wiley.com/doi/10.1002/cpt196896819/abstract

Cephaloridine (or cefaloridine) is a first generation semisynthetic derivative of cephalosporin C. It is unique among cephalosporins in that it exists as a zwitterion. It is of semi synthetic origin and belongs to cephem carboxylate. It belongs to Peptidoglycan synthesis inhibitor pharmacological group on the basis of mechanism of action. Since the discovery of cephalosporins P, N and C in 1948 there have been many studies describing the antibiotic action of cephalosporins and the possibility to synthesize derivatives. Hydrolysis of cephalosporin C, isolation of 7-aminocephalosporanic acid and the addition of side chains opened the possibility to produce various semi-synthetic cephalosporins. In 1962, cephalothin and cephaloridine were introduced. Cephaloridine is very active against gram positive cocci and used in a large variety of bacterial infections, such as respiratory tract, skin and urinary tract infections. Cephaloridine is primarily indicated in conditions like Bacterial infections, Bronchitis, Gonorrhoea, and can also be given in adjunctive therapy as an alternative drug of choice in Corneal ulcers, Intraocular infections. Cephaloridine was temporarily popular because it was better tolerated intramuscularly and attained in higher and more sustained levels in blood than cephalothin. Because it is also poorly absorbed after oral administration the use of this drug for humans declined rapidly, especially since the second generation of cephalosporins was introduced in the 1970s. Today it is more commonly used in veterinary practice to treat mild to severe bacterial infections caused by penicillin resistant and penicillin sensitive Staphylococcus aureus, Escherichia coli, Streptococcus pyogenes, Streptococcus pneumoniae, Bacillus sutbtilis, Klebsiella, Clostridium diptheriae, Salmonella and Shigella. Before the 1970s, cephaloridine was used to treat patients with urinary tract infections. Besides the drug has been used successfully in the treatment of various lower respiratory tract infections. Cephaloridine was very effective to cure pneumococcal pneumonia. It has a high clinical and bacteriological rate of success in staphylococcal and streptococcal infections.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
D-alanyl-D-alanine carboxypeptidase DacC 3 Target ID: P39844 Gene ID: 939990.0 Gene Symbol: dacC Target Organism: Bacillus subtilis (strain 168) Sources: http://www.ncbi.nlm.nih.gov/pubmed/11160090	Inhibitor 8504
Rabbit proximal tubules 1 Target ID: Rabbit proximal tubules Sources: http://www.ncbi.nlm.nih.gov/pubmed/2068729	Inhibitor 8504	1.1 mM [EC50]
Solute carrier family 22 member 5 3 Target ID: CHEMBL2073693 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10636865	Inhibitor 8504	0.23 mM [IC50]
Solute carrier family 22 member 6 19 Target ID: CHEMBL1641347 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10929807	Inhibitor 8504	1250.0 µM [IC50]
Solute carrier family 22 member 7 5 Target ID: CHEMBL1955711 Sources: http://www.ncbi.nlm.nih.gov/pubmed/12650826	Inhibitor 8504	4.48 mM [IC50]
Escherichia coli growth 23 Target ID: Escherichia coli growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/18765691	Inhibitor 8504
Peptidoglycan biosynthesis 20 Target ID: map00550 Sources: http://www.kegg.jp/entry/D01075	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Respiratory tract infections 85 Sources: http://www.medclik.com/General/pages/Drugmanual/BrandSearch9/CEPORAN.asp	Curative	Approved 8583	Ceporan Approved Use Respiratory tract infections, Septicemia, Skin & Soft tissue infections, Urinary tract & genital tract infections, Surgical prophylaxis
Urinary tract infections 207 Sources: http://drugbook.in/ceporan-500mg.html	Curative	Approved 8583	Ceporan Approved Use Respiratory tract infections, Septicemia, Skin & Soft tissue infections, Urinary tract & genital tract infections, Surgical prophylaxis
Sepsis 74 Sources: http://www.medclik.com/General/pages/Drugmanual/BrandSearch9/CEPORAN.asp	Curative	Approved 8583	Ceporan Approved Use Respiratory tract infections, Septicemia, Skin & Soft tissue infections, Urinary tract & genital tract infections, Surgical prophylaxis

C_max

Value	Dose	Co-administered	Analyte	Population
38 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/278145/	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:		CEPHALORIDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
40 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/278145/	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:		CEPHALORIDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/278145/	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:		CEPHALORIDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
69% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/278145/	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:		CEPHALORIDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT2 153 PEPT1 27 OAT1 725 OAT3 747 OAT4 150 OCTN2 71	OCTN2 59 OAT1 395 OAT3 391

Drug as perpetrator

Target	Modality	Activity
OCTN2 71	inhibitor 4027 Sources: http://transportal.compbio.ucsf.edu/compounds/cephaloridine/, https://www.jbc.org/article/S0021-9258(18)31098-6/fulltext	yes [IC50 230 uM]
OAT2 155	inhibitor 4027 Sources: https://pubs.rsc.org/EN/content/chapterhtml/2015/bk9781849738286-00001?isbn=978-1-84973-828-6&sercode=bk, http://transportal.compbio.ucsf.edu/compounds/cephaloridine/, https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [IC50 4480 uM]
OAT3 749	inhibitor 4027 Sources: http://transportal.compbio.ucsf.edu/compounds/cephaloridine/, https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [Ki 2460 uM]
OAT4 150	inhibitor 4027 Sources: http://transportal.compbio.ucsf.edu/compounds/cephaloridine/, https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [Ki 3630 uM]
OAT1 730	inhibitor 4027 Sources: http://transportal.compbio.ucsf.edu/compounds/cephaloridine/, https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [Ki 740 uM]
PEPT1 29	inhibitor 4027 Sources: https://pubs.rsc.org/EN/content/chapterhtml/2015/bk9781849738286-00001?isbn=978-1-84973-828-6&sercode=bk	yes

Drug as victim

Target	Modality	Activity
OAT1 395	substrate 4014 Sources: https://www.taylorfrancis.com/books/principles-biochemical-toxicology-john-timbrell/10.3109/9781420007084, https://go.drugbank.com/drugs/DB09008, https://pubmed.ncbi.nlm.nih.gov/19953504/ Page: 332-335	yes
OAT3 391	substrate 4014 Sources: https://go.drugbank.com/drugs/DB09008, https://pubmed.ncbi.nlm.nih.gov/19953504/	yes
OCTN2 59	substrate 4014 Sources: https://www.annualreviews.org/doi/abs/10.1146/annurev.pharmtox.44.101802.121444	yes

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L1L3T
Ambinter	Amb23401101	http://www.ambinter.com/reference/23401101
AmicBase - Antimicrobial Activities	5138
Aurora Fine Chemicals LLC	A17.918.340	http://online.aurorafinechemicals.com/info?ID=A17.918.340
BenchChem	B523063	https://www.benchchem.com/product/b523063
BePharm Ltd.	B120380
BOC Sciences	50-59-9
Chemieliva Pharmaceutical Co., Ltd	PBCM0603728
Chemspace	CSSB00020627542	https://chem-space.com/CSSB00020627542
Compound Cloud	5773
Compound Cloud	5774
eMolecules	106943421
eMolecules	46015071
eMolecules	50221528
eNovation Chemicals	D676125	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676125
Hairui	HR143713	http://www.hairuichem.com/en/product/50-59-9.html
mcule	MCULE-8657732741
MuseChem	I005918
Norris Pharm	NSZB-A011214
NovoSeek	5773
Oxchem Corporation	AX8120380
PI Chemicals	PI-39101
Smolecule	S523063	http://www.smolecule.com/products/s523063
Smolecule	S772632	https://www.smolecule.com/products/s772632
THE BioTek	bt-263294	https://www.thebiotek.com/product/inhibitors/bt-263294
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-0142
ZINC	ZINC000001532351	http://zinc15.docking.org/substances/ZINC000001532351
ZINC	ZINC000003202698	http://zinc15.docking.org/substances/ZINC000003202698
ZINC	ZINC000003202700	http://zinc15.docking.org/substances/ZINC000003202700
ZINC	ZINC000003202703	http://zinc15.docking.org/substances/ZINC000003202703

PubMed

Title	Date	PubMed
In vitro and in vivo efficacy of β-lactams against replicating and slowly growing/nonreplicating Mycobacterium tuberculosis.	2013-06	23507276
Kidney injury molecule-1 expression in rat proximal tubule after treatment with segment-specific nephrotoxicants: a tool for early screening of potential kidney toxicity.	2010-04	20305092
Transcriptomic analysis of nephrotoxicity induced by cephaloridine, a representative cephalosporin antibiotic.	2008-06	18500788
In vitro gene expression analysis of nephrotoxic drugs in rat primary renal cortical tubular cells.	2008-03	18172885
Serum thymic factor, FTS, attenuates cisplatin nephrotoxicity by suppressing cisplatin-induced ERK activation.	2005-11-01	16154539
Protective effect of serum thymic factor, FTS, on cephaloridine-induced nephrotoxicity in rats.	2005-11	16272694
Effect of ginsenoside-Rd in cephaloridine-induced renal disorder.	1999-02	9933756
Magnesium lithospermate B ameliorates cephaloridine-induced renal injury.	1997-12	9455678
Can penicillins and other beta-lactam antibiotics be used to treat tuberculosis?	1995-12	8592990
[Studies on the mechanisms of renal damages induced by nephrotoxic compounds].	1995-12	8583688
Suppressed expression of calcium-binding protein regucalcin mRNA in the renal cortex of rats with chemically induced kidney damage.	1995-10-04	8584014
Glucocorticoid amelioration of nephrotoxicity: a study of cephaloridine-methylprednisolone interaction in the rat.	1995-07	7576815
Cephaloridine nephrotoxicity in diabetic rats: modulation by insulin treatment.	1995-06-26	7624867
Preventive effect of betamipron on nephrotoxicity and uptake of carbapenems in rabbit renal cortex.	1994-09	7861655
Effects of KW-3902, a novel adenosine A1-receptor antagonist, on cephaloridine-induced acute renal failure in rats.	1994-01	8164396
[Study on gamma-GTP activity in urine and renal tissue of drug-induced nephrotoxicity in rats].	1993-07	8102655
Methimazole protection of rats against chemically induced kidney damage in vivo.	1992-01	1731048
Drugs as allergens: an immunoassay for detecting IgE antibodies to cephalosporins.	1990	2083978
Safety evaluation of meropenem in animals: studies on the kidney.	1989-09	2681127
[Acute renal failure caused by ceporin, kanamycin and gentamicin].	1989-03-01	2728142
Relieving effect of saline on cephaloridine nephrotoxicity in rats.	1989-03	2752494
The use of renal cortical slices from the Fischer 344 rat as an in vitro model to evaluate nephrotoxicity.	1988-07	2905310
Protective effect of piperacillin against nephrotoxicity of cephaloridine and gentamicin in animals.	1988-06	3415211
[Nephrotoxicity of cefodizime sodium in rats--single and 14-day repeated intravenous administration].	1988-06	3172294
Biochemical mechanisms of cephaloridine nephrotoxicity.	1988	3285106
Neurotoxicity of beta-lactam antibiotics. Experimental kinetic and neurophysiological studies.	1988	3241957
Vasopressin-resistant polyuria induced by cephaloridine administration in rats.	1986	3829983
Ceftazidime nephrotoxicity in rats.	1984-04	6375559
Lipid peroxidation: a possible mechanism of cephaloridine-induced nephrotoxicity.	1983-01	6845359
[Studies on the nephrotoxicity of cephaloridine in the mouse (author's transl)].	1982	7201831
In vitro and in vivo susceptibility of atypical mycobacteria to various drugs.	1981-09-01	7339820
Nephrotoxicity of cefotiam (CGP 14221/E) in rats and rabbits.	1981-09	6271094
Renal tolerance of ceftazidime in animals.	1981-09	19802993
Cephaloridine encephalopathy.	1981-08-08	6789989
IgE antibodies for penicillins and cephalosporins in rats. III. Antigenic specificity of rat anti-cephalosporin-OvA IgE sera.	1981-01	6166604
Renal tubular necrosis following cephalothin.	1979	471144
Drug-induced lysosomal changes and nephrotoxicity in rats.	1978-11	735819
Renal and hepatic necrosis after metabolic activation of 2-substituted furans and thiophenes, including furosemide and cephaloridine.	1977-11	595008
Molecular basis for several drug-induced nephropathies.	1977-04	851123
[Acute renal failure following combined cephaloridine-gentamycin therapy (author's transl)].	1973-12-21	4589000
Relative nephrotoxicity of cephalosporin antibiotics in an animal model.	1972-09-09	5074752
Nephrotoxicity and acute renal failure associated with cephalothin and cephaloridine.	1971-11	5289757
Nephrotoxicity of cephaloridine.	1971-10-09	5097409
Parkinsonism syndrome due to cephaloridine.	1971-05-17	5108409
Reversible encephalopathy and acute renal failure after cephaloridine.	1970-10-31	5475848
The nephrotoxicity of cephaloridine.	1970-10	5488206
[Nephrotoxicity of cephaloridine. 3 cases of acute renal failure with anuria].	1969-10-18	4982004
Renal damage associated with prolonged administration of ampicillin, cephaloridine, and cephalothin.	1969	5396519
Penicillin-induced haemolytic anaemia.	1968-07-06	5661907
Nephrotoxicity associated with the use of cephaloridine.	1967-05-22	6071504

Patents

Sample Use Guides

In Vivo Use Guide

1gm to1.5gm daily in two or three divided doses I.M. or I.V. In severe infections: 1.5 gm 8 hourly or 12 hourly. Children: 15 to 30 mg/kg/d.

Route of Administration: Intramuscular

In Vitro Use Guide

Against meningococci cephaloridine inactivated all strains at concentrations below 0.5 ug/ml

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:54:43 GMT 2025` Edited by `admin` on `Mon Mar 31 17:54:43 GMT 2025`
Record UNII	LVZ1VC61HB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFALORIDINE

Preferred Name

English

CEPHALORIDINE

Official Name

English

CEPHALORIDINE [MI]

Common Name

English

CEPHALORIDINE [USAN]

Common Name

English

CEPHALORIDINE [HSDB]

Common Name

English

7-(.ALPHA.-(2-THIENYL)ACETAMIDO)-3-(1-PYRIDYLMETHYL)-3-CEPHEM-4-CARBOXYLIC ACID BETAINE

Common Name

English

CEFALORIDINE [MART.]

Common Name

English

CEFALORIDINE [JAN]

Common Name

English

Cefaloridine [WHO-DD]

Common Name

English

cefaloridine [INN]

Common Name

English

40602

Code

English

PYRIDINIUM, 1-((2-CARBOXY-8-OXO-7-((2-THIENYLACETYL)AMINO)-5-THIA-1-AZABICYCLO(4.2.0)-OCT-2-EN-3-YL)METHYL)-, HYDROXIDE, INNER SALT, (6R-TRANS)-

Common Name

English

((6R,7R)-1-((2-CARBOXY-8-OXO-7-(2-(2-THIENYL)ACETAMIDO)-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)PYRIDINIUM HYDROXIDE, INNER SALT

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01DB02