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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17N3O4S2
Molecular Weight 415.4889
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEPHALORIDINE

SMILES

c1cc[n+](cc1)CC2=C(C(=O)[O-])N3C(=O)[C@]([H])([C@@]3([H])SC2)N=C(Cc4cccs4)O

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 415.4889
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Curator's Comment:: CNS penetrant in humans

Originator

Curator's Comment:: Retrieved from Glaxo: A History to 1962 By R. P. T. Davenport-Hines, Judy Slinn, p.196 Cephaloridine (Ceporin) was launched in 1964 by Glaxo

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P39844
Gene ID: 939990.0
Gene Symbol: dacC
Target Organism: Bacillus subtilis (strain 168)
Target ID: Rabbit proximal tubules
1.1 mM [EC50]
0.23 mM [IC50]
1250.0 µM [IC50]
4.48 mM [IC50]
Target ID: Escherichia coli growth
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Ceporan

Approved Use

Respiratory tract infections, Septicemia, Skin & Soft tissue infections, Urinary tract & genital tract infections, Surgical prophylaxis
Curative
Ceporan

Approved Use

Respiratory tract infections, Septicemia, Skin & Soft tissue infections, Urinary tract & genital tract infections, Surgical prophylaxis
Curative
Ceporan

Approved Use

Respiratory tract infections, Septicemia, Skin & Soft tissue infections, Urinary tract & genital tract infections, Surgical prophylaxis
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
38 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
40 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.5 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
69%
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer









Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Nephrotoxicity associated with the use of cephaloridine.
1967 May 22
Penicillin-induced haemolytic anaemia.
1968 Jul 6
Renal damage associated with prolonged administration of ampicillin, cephaloridine, and cephalothin.
1969
[Nephrotoxicity of cephaloridine. 3 cases of acute renal failure with anuria].
1969 Oct 18
The nephrotoxicity of cephaloridine.
1970 Oct
Reversible encephalopathy and acute renal failure after cephaloridine.
1970 Oct 31
Parkinsonism syndrome due to cephaloridine.
1971 May 17
Nephrotoxicity and acute renal failure associated with cephalothin and cephaloridine.
1971 Nov
Nephrotoxicity of cephaloridine.
1971 Oct 9
Relative nephrotoxicity of cephalosporin antibiotics in an animal model.
1972 Sep 9
[Acute renal failure following combined cephaloridine-gentamycin therapy (author's transl)].
1973 Dec 21
Convulsion following intrathecal cephaloridine.
1975
Cephaloridine, cephalothin and the kidney.
1975
Acute renal failure associated with cephalosporin therapy.
1975 Jun
Molecular basis for several drug-induced nephropathies.
1977 Apr
Renal and hepatic necrosis after metabolic activation of 2-substituted furans and thiophenes, including furosemide and cephaloridine.
1977 Nov
Drug-induced lysosomal changes and nephrotoxicity in rats.
1978 Nov
Renal tubular necrosis following cephalothin.
1979
Cephaloridine encephalopathy.
1981 Aug 8
IgE antibodies for penicillins and cephalosporins in rats. III. Antigenic specificity of rat anti-cephalosporin-OvA IgE sera.
1981 Jan
Nephrotoxicity of cefotiam (CGP 14221/E) in rats and rabbits.
1981 Sep
Renal tolerance of ceftazidime in animals.
1981 Sep
In vitro and in vivo susceptibility of atypical mycobacteria to various drugs.
1981 Sep-Oct
[Studies on the nephrotoxicity of cephaloridine in the mouse (author's transl)].
1982
Lipid peroxidation: a possible mechanism of cephaloridine-induced nephrotoxicity.
1983 Jan
Ceftazidime nephrotoxicity in rats.
1984 Apr
Vasopressin-resistant polyuria induced by cephaloridine administration in rats.
1986
Biochemical mechanisms of cephaloridine nephrotoxicity.
1988
Neurotoxicity of beta-lactam antibiotics. Experimental kinetic and neurophysiological studies.
1988
The use of renal cortical slices from the Fischer 344 rat as an in vitro model to evaluate nephrotoxicity.
1988 Jul
Protective effect of piperacillin against nephrotoxicity of cephaloridine and gentamicin in animals.
1988 Jun
[Nephrotoxicity of cefodizime sodium in rats--single and 14-day repeated intravenous administration].
1988 Jun
Relieving effect of saline on cephaloridine nephrotoxicity in rats.
1989 Mar
[Acute renal failure caused by ceporin, kanamycin and gentamicin].
1989 Mar-Apr
Safety evaluation of meropenem in animals: studies on the kidney.
1989 Sep
Drugs as allergens: an immunoassay for detecting IgE antibodies to cephalosporins.
1990
Cephaloridine nephrotoxicity is potentiated by selenium deficiency but not copper deficiency in rats.
1992 Jun
[Study on gamma-GTP activity in urine and renal tissue of drug-induced nephrotoxicity in rats].
1993 Jul
Effects of KW-3902, a novel adenosine A1-receptor antagonist, on cephaloridine-induced acute renal failure in rats.
1994 Jan
Preventive effect of betamipron on nephrotoxicity and uptake of carbapenems in rabbit renal cortex.
1994 Sep
Can penicillins and other beta-lactam antibiotics be used to treat tuberculosis?
1995 Dec
[Studies on the mechanisms of renal damages induced by nephrotoxic compounds].
1995 Dec
Glucocorticoid amelioration of nephrotoxicity: a study of cephaloridine-methylprednisolone interaction in the rat.
1995 Jul
Cephaloridine nephrotoxicity in diabetic rats: modulation by insulin treatment.
1995 Jun 26
Suppressed expression of calcium-binding protein regucalcin mRNA in the renal cortex of rats with chemically induced kidney damage.
1995 Oct 4
Magnesium lithospermate B ameliorates cephaloridine-induced renal injury.
1997 Dec
Effect of ginsenoside-Rd in cephaloridine-induced renal disorder.
1999 Feb
Enhancement of protein kinase C activity and chemiluminescence intensity in mitochondria isolated from the kidney cortex of rats treated with cephaloridine.
2002 Aug 1
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
2002 Nov
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 Apr
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Could be used intavenously
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 Sat Jun 26 14:31:46 UTC 2021
Edited
by admin
on Sat Jun 26 14:31:46 UTC 2021
Record UNII
LVZ1VC61HB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEPHALORIDINE
HSDB   MI   USAN  
USAN  
Official Name English
CEFALORIDINE
INN   JAN   MART.   WHO-DD  
INN  
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
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
NCI_THESAURUS C357
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
WHO-ATC J01DB02
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
Code System Code Type Description
DRUG CENTRAL
573
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY
PUBCHEM
5773
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY
INN
1910
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY
EVMPD
SUB06169MIG
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY
RXCUI
2233
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
CEPHALORIDINE
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY
MESH
D002509
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY
NCI_THESAURUS
C76594
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY
DRUG BANK
DB09008
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY
HSDB
3023
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY
CAS
50-59-9
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY
MERCK INDEX
M1065
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
200-052-6
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY
FDA UNII
LVZ1VC61HB
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY
EPA CompTox
50-59-9
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY
ChEMBL
CHEMBL316157
Created by admin on Sat Jun 26 14:31:46 UTC 2021 , Edited by admin on Sat Jun 26 14:31:46 UTC 2021
PRIMARY
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