CEFPIRAMIDE SODIUM

US Previously Marketed

First approved in 1989

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H23N8O7S2.Na
Molecular Weight	634.619
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[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=RIWWMGQFMUUYIY-ALLHVENQSA-M

InChI=1S/C25H24N8O7S2.Na/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);/q;+1/p-1/t17-,18-,23-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C25H23N8O7S2
Molecular Weight	611.63
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
[Comparative study of cefpiramide + amikacin versus piperacillin + amikacin in granulocytopenic patients: a randomized, prospective study].	1992 Aug	1503486
[Cefpiramide (Tamicin) in the treatment of purulent complications of abdominal surgery].	1995 Sep	8651827
In-vitro antibacterial activities of cefpiramide and other broad-spectrum antibiotics against 440 clinical isolates in China.	2000 Jun	11810540
Quantitative evaluation of capacity-limited hepatobiliary transport based on hepatocellular diffusion model by MULTI(FEM).	2001 Oct	11768289
Biliary excretion of tauroursodeoxycholate-3-sulfate in the rat.	2001 Sep	11546558
Biliary excretion of olmesartan, an anigotensin II receptor antagonist, in the rat.	2005 May	15853995
Inflammatory pseudotumor of the liver treated by hepatic resection: a case report.	2006 Feb 28	16502497
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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:24:19 GMT 2023` Edited by `admin` on `Fri Dec 15 15:24:19 GMT 2023`
Record UNII	137KB7GYKB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFPIRAMIDE SODIUM

Official Name

English

CEFPIRAMIDE SODIUM [MART.]

Common Name

English

CEFPIRAMIDE SODIUM SALT [MI]

Common Name

English

CEFPIRAMIDE SODIUM [JAN]

Common Name

English

WY-44635 SODIUM

Code

English

SUNCEFAL

Brand Name

English

SODIUM (6R,7R)-7-((R)-2-(4-HYDROXY-6-METHYLNICOTINAMIDO)-2-(P-HYDROXYPHENYL)ACETAMIDO)-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLATE

Common Name

English

CEFPIRAMIDE SODIUM SALT

Common Name

English

WY-44,635 SODIUM

Code

English

Cefpiramide sodium [WHO-DD]

Common Name

English

CEFPIRAMIDE SODIUM [USAN]

Common Name

English

CEFPIRAMIDE SODIUM [ORANGE BOOK]

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((((4-HYDROXY-6-METHYL-3-PYRIDINYL)CARBONYL)AMINO)(4-HYDROXYPHENYL)ACETYL)AMINO)-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-, (6R-(6.ALPHA.,7.BETA.(R*)))

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357