BETAMIPRON

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H11NO3
Molecular Weight	193.1992
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CCNC(=O)C1=CC=CC=C1

InChI

InChIKey=CWXYHOHYCJXYFQ-UHFFFAOYSA-N

InChI=1S/C10H11NO3/c12-9(13)6-7-11-10(14)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,14)(H,12,13)

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Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/7861655
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/10211864 http://www.ncbi.nlm.nih.gov/pubmed/11426832 http://www.ncbi.nlm.nih.gov/pubmed/12023506

Betamipron (BP) is an amino acid derivative that has benzoyl and carboxyl groups in its structure, and it also has very low toxicity in mammals (LD50 in the rat, more than 3,000 mg/kg, i.v.). BP is a renal anionic transport inhibitor and decreases nephrotoxicity caused by high doses of carbapenems, anionic drugs, by inhibiting the drug accumulation in the renal cortex. BP significantly inhibited organic anion uptake by human organic anion transporter 1 (human-OAT1) and human-OAT3 in a dose-dependent manner. Panipenem-betamipron is marketed as Carbenin® (Sankyo Company, Tokyo, Japan).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Solute carrier family 22 member 6 19 Target ID: Q4U2R8\|\|\|Q9NQC2 Gene ID: 9356.0 Gene Symbol: SLC22A6 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/11426832	Inhibitor 8297		23.6 µM [Ki]
Solute carrier family 22 member 8 17 Target ID: Q8TCC7 Gene ID: 9376.0 Gene Symbol: SLC22A8 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/11426832	Inhibitor 8297		48.3 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1518122	Secondary		Approved 8429	Carbenin Approved Use Unknown Launch Date 1993

PubMed

Title	Date	PubMed
Preventive effect of betamipron on nephrotoxicity and uptake of carbapenems in rabbit renal cortex.	1994 Sep	7861655
Effects of betamipron on cisplatin nephrotoxicity and its pharmacokinetics in rats.	1997 Apr	9145215
Betamipron reduces cisplatin nephrotoxicity in rodents without modifying its antileukemic activity in mice.	1997 May	9154659
Nephroprotective effect of betamipron on a new carbapenem, DA-1131, in rabbits.	1999 Apr	10211864
Characterization of organic anion transport inhibitors using cells stably expressing human organic anion transporters.	2001 May 11	11426832
Interaction of human organic anion transporters 2 and 4 with organic anion transport inhibitors.	2002 Jun	12023506
Pharmacokinetics of 3-[125I]iodo-alpha-methyl-L-tyrosine, a tumor imaging agent, after probenecid loading in mice implanted with colon cancer DLD-1 cells.	2007 Nov	17998105

Patents

Sample Use Guides

In Vivo Use Guide

Intravenous drip infusion of either 10 mg/10 mg/kg or 20 mg/20 mg/kg of Panipenem/betamipron (PAPM/BP) for 30 minutes.

Route of Administration: Intravenous

In Vitro Use Guide

S2 hOAT2 cells were incubated in a medium containing 50 nM [3H]PGF2 at 37C for 2 min in the absence or presence of 1 mM betamipron, and the effect of the drug in PGF2 uptaked was studied. Inhibition of ES uptake by hOAT4 was measured at 500 uM of the drug.

Name

Type

Language

BETAMIPRON

Official Name

English

CS-443

Code

English

NSC-192714

Code

English

BETAMIPRON [JAN]

Common Name

English

Betamipron [WHO-DD]

Common Name

English

BETAMIPRON [MI]

Common Name

English

BETAMIPRON [MART.]

Common Name

English

N-BENZOYL-.BETA.-ALANINE

Systematic Name

English

betamipron [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C283