CEFPIRAMIDE

US Previously Marketed

First approved in 1989

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H24N8O7S2
Molecular Weight	612.637
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)C4=CN=C(C)C=C4O)C5=CC=C(O)C=C5)C(O)=O

InChI

InChIKey=PWAUCHMQEXVFJR-PMAPCBKXSA-N

InChI=1S/C25H24N8O7S2/c1-11-7-16(35)15(8-26-11)20(36)27-17(12-3-5-14(34)6-4-12)21(37)28-18-22(38)33-19(24(39)40)13(9-41-23(18)33)10-42-25-29-30-31-32(25)2/h3-8,17-18,23,34H,9-10H2,1-2H3,(H,26,35)(H,27,36)(H,28,37)(H,39,40)/t17-,18-,23-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6983860 | https://www.ncbi.nlm.nih.gov/pubmed/6601470

Cefpiramide or SM-1652 (sodium 7-[D(-)-alpha-(4-hydroxy-6-methylpyridine-3-carboxamido)-alpha-(4-hydroxyphenyl)acetamido]-3-[(1-methyl-1H-tetrazol-5-yl) thiomethyl]-3-cephem-4-carboxylate) is a semisynthetic cephalosporin derivative with a broad spectrum of antibacterial activity. This antibiotic has been reported to have potent in vitro and in vivo antibacterial activities against gram-positive and -negative bacteria.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: http://www.kegg.jp/entry/D03428	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3141169 https://www.ncbi.nlm.nih.gov/pubmed/6983860 https://www.ncbi.nlm.nih.gov/pubmed/6601470	Curative		Approved 8429	CEFPIRAMIDE SODIUM Approved Use This medication may be used in susceptible infections. Launch Date 1989

AUC

Value	Dose	Analyte	Population
1300 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8198940	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFPIRAMIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1598 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2007321	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFPIRAMIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
672 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1686912	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFPIRAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
672 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8198940	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFPIRAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8198940	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFPIRAMIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
13.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2007321	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFPIRAMIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1686912	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFPIRAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
5.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8198940	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFPIRAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
10.4% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2007321	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIRAMIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1686912	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:		CEFPIRAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 g single, intravenous Highest studied dose Dose: 2 g Route: intravenous Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/3435107	unhealthy, 42 years (range: 18 to 62 years) n = 30 Health Status: unhealthy Age Group: 42 years (range: 18 to 62 years) Sex: M+F Population Size: 30 Sources: https://pubmed.ncbi.nlm.nih.gov/3435107	Sources: https://pubmed.ncbi.nlm.nih.gov/3435107
500 mg 2 times / day multiple, intramuscular Highest studied dose Dose: 500 mg, 2 times / day Route: intramuscular Route: multiple Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6655847	unhealthy n = 8 Health Status: unhealthy Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/6655847	Sources: https://pubmed.ncbi.nlm.nih.gov/6655847

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	OATP1B1/3 11

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OATP1B1/3 11	substrate 3367 Sources: https://dmd.aspetjournals.org/content/41/2/372/tab-figures-data	likely

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7845504/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:59213	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59213
ChemicalBook	CB5265046	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5265046
MolPort	MolPort-023-220-334	https://www.molport.com/shop/molecule-link/MolPort-023-220-334
ZINC	ZINC000004215257	http://zinc15.docking.org/substances/ZINC000004215257
eMolecules	26951180	https://www.emolecules.com/cgi-bin/more?vid=26951180

PubMed

Title	Date	PubMed
[Cefpiramide (Tamicin) in the treatment of purulent complications of abdominal surgery].	1995 Sep	8651827
Biliary excretion of tauroursodeoxycholate-3-sulfate in the rat.	2001 Sep	11546558
Long level (t4-l1) spinal epidural abscess in a diabetic patient - a case report -.	2008 Jun	20411144
Involvement of multidrug resistance-associated protein 2 (Abcc2) in molecular weight-dependent biliary excretion of beta-lactam antibiotics.	2008 Jun	18339814
The efficacy of postoperative prophylactic antibiotics in orthognathic surgery: a prospective study in Le Fort I osteotomy and bilateral intraoral vertical ramus osteotomy.	2009 Feb 28	19259349
Antibiotic and synergistic effect of Leu-Lys rich peptide against antibiotic resistant microorganisms isolated from patients with cholelithiasis.	2010 Sep 3	20682287

Patents

Sample Use Guides

In Vivo Use Guide

1-2 gm daily in 2 divided doses by inj.

Route of Administration: Parenteral

In Vitro Use Guide

As judged by the MIC50 and the MIC90 values, cefpiramide was one of the most active cephalosporins against Pseudomonas aeruginosa (MIC50 2.9 micrograms/ml, MIC90 64 micrograms/ml), staphylococci (MIC50 1.2 micrograms/ml, MIC90 10 micrograms/ml) and Enterococcus faecalis (MIC50 13 micrograms/ml, MIC90 43 micrograms/ml). Cefpiramide had moderate activity against Enterobacteriaceae (MIC50 4 micrograms/ml, MIC90 108 micrograms/ml), comparable to that of the older second-generation cephalosporins.

Name

Type

Language

CEFPIRAMIDE

Official Name

English

cefpiramide [INN]

Common Name

English

WY-44,635

Code

English

CEFPIRAMIDE [USP IMPURITY]

Common Name

English

CEFPIRAMIDE [MI]

Common Name

English

CEFPIRAMIDE [USP-RS]

Common Name

English

WY-44635

Code

English

Cefpiramide [WHO-DD]

Common Name

English

CEFPIRAMIDE [USAN]

Common Name

English

NSC-759869

Code

English

CEFPIRAMIDE [MART.]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J01DD11