BROVINCAMINE FUMARATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H25BrN2O3.C4H4O4
Molecular Weight	549.411
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.CC[C@@]12CCCN3CCC4=C([C@H]13)N(C5=CC(Br)=CC=C45)[C@](O)(C2)C(=O)OC

InChI

InChIKey=CKCVTPQYFOMHFD-HPJCWFBOSA-N

InChI=1S/C21H25BrN2O3.C4H4O4/c1-3-20-8-4-9-23-10-7-15-14-6-5-13(22)11-16(14)24(17(15)18(20)23)21(26,12-20)19(25)27-2;5-3(6)1-2-4(7)8/h5-6,11,18,26H,3-4,7-10,12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t18-,20+,21+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Molecular Formula	C21H25BrN2O3
Molecular Weight	433.339
Charge	0
Count

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

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/8851150

Brovincamine also known as brovincamine fumarate (BV, Sabromin) was used in Japan mainly as an improver of cerebral circulation and metabolism, and also as an inhibitor of the aggregation of platelets through the cyclic AMP pathway in patients with normal tension glaucoma. Brovincamine exerts its action via calcium channels blockade. The current drug status is unknown.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Calcium channels 2 Target ID: Calcium channels Sources: http://www.ncbi.nlm.nih.gov/pubmed/4006317	Blocker 555

Conditions

Condition	Modality	Targets	Highest Phase	Product
Normal tension glaucoma 2 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10209728	Primary		Approved 8583	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
3 μg/mL/(mg dose/kg) EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7169608/	0.5 mg/kg single, oral dose: 0.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		[3H]-11-BROMOVINCAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
1900 ng × eq/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4085521/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:		[3H]-11-BROMOVINCAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
28 μg × h/mL/(mg dose/kg) EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7169608/	0.5 mg/kg single, oral dose: 0.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		[3H]-11-BROMOVINCAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
17 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7169608/	0.5 mg/kg single, oral dose: 0.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		[3H]-11-BROMOVINCAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
11 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4085521/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:		[3H]-11-BROMOVINCAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
3% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7169608/	0.5 mg/kg single, oral dose: 0.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		[3H]-11-BROMOVINCAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

Doses

Dose	Population	Adverse events
40 mg single, oral Studied dose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: https://pubmed.ncbi.nlm.nih.gov/4085521/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/4085521/	Sources: https://pubmed.ncbi.nlm.nih.gov/4085521/

PubMed

Title	Date	PubMed
Use of calcium channel blockers for glaucoma.	2011-01	20933604
Inhibitory action of brovincamine on catecholamine secretion from cultured bovine adrenal medullary cells: possible relation to its blocking action on Ca2+ channels.	1991-06-21	2069593
Effects of brovincamine on the stereological parameters of corticocerebral capillaries.	1987-03-09	3821365
Cardiovascular effects of brovincamine and possible mechanisms involved.	1985-03-01	4006317
Calcium antagonistic action involved in vasodilation by brovincamine.	1984	6698382
The metabolic fate of 11-bromo-[15-3H] vincamine in rats, dogs and humans.	1982-12	7169608
Determination of 11-bromovincamine in human plasma by high-performance liquid chromatography.	1982-03-12	7076771

Patents

Sample Use Guides

In Vivo Use Guide

20 mg three times daily.

Route of Administration: Oral

In Vitro Use Guide

Possible mode of vasodilative action of brovincamine was assessed in isolated cardiovascular preparations in comparison with verapamil and papaverine. Brovincamine (IC50: 1.2 x 10(-5)M) caused a dose-dependent relaxation of potassium (30 mM)-contracture in the rabbit pulmonary arterial segment. This relaxation was antagonized by increasing external Ca2+ concentration to 12.4 mM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:30:13 GMT 2025` Edited by `admin` on `Mon Mar 31 19:30:13 GMT 2025`
Record UNII	Y3SNC78UTU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BROVINCAMINE FUMARATE

Common Name

English

BROVINCAMINE HYDROGEN FUMARATE

Preferred Name

English

BROVINCAMINE HYDROGEN FUMARATE [MI]

Common Name

English

Brovincamine fumarate [WHO-DD]

Common Name

English

BROVINCAMINE FUMARATE [JAN]

Common Name

English

EBURNAMENINE-14-CARBOXYLIC ACID, 14,15-DIHYDRO-11-BROMO-14-HYDROXY-, METHYL ESTER, (3-.ALPHA.,14-.BETA.,16-.ALPHA.)-, (E)-2-BUTENEDIOATE (1:1) (SALT)

Common Name

English

Code System Code Type Description

SMS_ID

100000085144