U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of BETAMIPRON

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)

HIDE SMILES / InChI

Molecular Formula C10H11NO3
Molecular Weight 193.1992
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Curator's Comment: Panipenem-betamipron is marketed as Carbenin (Sankyo Company, Tokyo, Japan).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q4U2R8|||Q9NQC2
Gene ID: 9356.0
Gene Symbol: SLC22A6
Target Organism: Homo sapiens (Human)
23.6 µM [Ki]
Target ID: Q8TCC7
Gene ID: 9376.0
Gene Symbol: SLC22A8
Target Organism: Homo sapiens (Human)
48.3 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Carbenin

Approved Use

Unknown

Launch Date

1993
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.25 μg/mL
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
15.59 μg/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
23.68 μg/mL
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.47 μg/mL
125 mg single, intravenous
dose: 125 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
14.1 μg/mL
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
16.19 μg/mL
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
33.23 μg/mL
1000 mg 2 times / day multiple, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
25.69 μg/mL
1000 mg 2 times / day multiple, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
18.33 μg/mL
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
38.74 μg/mL
20 mg/kg single, intravenous
dose: 20 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
50.08 μg/mL
30 mg/kg single, intravenous
dose: 30 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
18.08 μg/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
20.46 μg/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
25.81 μg/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
53 μg/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
54.3 μg/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
8.9 μg × h/mL
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
19.7 μg × h/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
31.29 μg × h/mL
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
5.31 μg × h/mL
125 mg single, intravenous
dose: 125 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
17.7 μg × h/mL
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
19.47 μg × h/mL
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
42.09 μg × h/mL
1000 mg 2 times / day multiple, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
32.96 μg × h/mL
1000 mg 2 times / day multiple, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
20.4 μg × h/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
37.61 μg × h/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
194.67 μg × h/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
630 μg × h/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1898 μg × h/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.65 h
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
0.67 h
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
0.76 h
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
0.65 h
125 mg single, intravenous
dose: 125 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
0.81 h
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.71 h
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.78 h
1000 mg 2 times / day multiple, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.79 h
1000 mg 2 times / day multiple, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.51 h
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
0.47 h
20 mg/kg single, intravenous
dose: 20 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
0.63 h
30 mg/kg single, intravenous
dose: 30 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
0.71 h
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.31 h
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.77 h
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.24 h
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
30.8 h
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
26.9%
1000 mg 2 times / day multiple, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
50.3%
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PANIPENEM
BETAMIPRON plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.5 g 1 times / 8 hours multiple, intravenous
Dose: 0.5 g, 1 times / 8 hours
Route: intravenous
Route: multiple
Dose: 0.5 g, 1 times / 8 hours
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
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.
2007-11
Interaction of human organic anion transporters 2 and 4 with organic anion transport inhibitors.
2002-06
Characterization of organic anion transport inhibitors using cells stably expressing human organic anion transporters.
2001-05-11
Nephroprotective effect of betamipron on a new carbapenem, DA-1131, in rabbits.
1999-04
Betamipron reduces cisplatin nephrotoxicity in rodents without modifying its antileukemic activity in mice.
1997-05
Effects of betamipron on cisplatin nephrotoxicity and its pharmacokinetics in rats.
1997-04
Preventive effect of betamipron on nephrotoxicity and uptake of carbapenems in rabbit renal cortex.
1994-09
Patents

Patents

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:06:33 GMT 2025
Edited
by admin
on Mon Mar 31 18:06:33 GMT 2025
Record UNII
3W0M245736
Record Status Validated (UNII)
Record Version
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Name Type Language
BETAMIPRON
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
CS-443
Preferred Name 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
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
WHO-ATC J01DH55
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
Code System Code Type Description
CAS
3440-28-6
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
PRIMARY
NSC
192714
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
PRIMARY
MERCK INDEX
m2453
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C72565
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PRIMARY
INN
6741
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
PRIMARY
ChEMBL
CHEMBL1231530
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
PRIMARY
WIKIPEDIA
BETAMIPRON
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
PRIMARY
FDA UNII
3W0M245736
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
PRIMARY
SMS_ID
100000085850
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
PRIMARY
PUBCHEM
71651
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
PRIMARY
MESH
C047207
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
PRIMARY
DRUG CENTRAL
355
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID0045626
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
PRIMARY
EVMPD
SUB05800MIG
Created by admin on Mon Mar 31 18:06:33 GMT 2025 , Edited by admin on Mon Mar 31 18:06:33 GMT 2025
PRIMARY
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