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Details

Stereochemistry RACEMIC
Molecular Formula C10H12N4O3
Molecular Weight 236.2273
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CARBAZOCHROME

SMILES

CN1CC(O)C2=C\C(=N\NC(N)=O)C(=O)C=C12

InChI

InChIKey=XSXCZNVKFKNLPR-SDQBBNPISA-N
InChI=1S/C10H12N4O3/c1-14-4-9(16)5-2-6(12-13-10(11)17)8(15)3-7(5)14/h2-3,9,16H,4H2,1H3,(H3,11,13,17)/b12-6-

HIDE SMILES / InChI

Molecular Formula C10H12N4O3
Molecular Weight 236.2273
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 1
Optical Activity ( + / - )

Description
Curator's Comment: Description is created based on several sources, including http://journal.publications.chestnet.org/article.aspx?articleID=1053722 and http://drugs-infos.blogspot.ru/2009/08/adona.html

Carbazochrome Sulfonic Acid is an antihemorrhagic, or hemostatic, agent that will cease blood flow by causing the aggregation and adhesion of platelets in the blood to form a platelet plug, ceasing blood flow from an open wound. It is hoped that this drug can be used in the future for preventing excessive blood flow during surgical operations and the treatment of hemorrhoids, but research on its effectiveness and the severity of possible side effects remains to be fairly inconclusive. Carbazochrome has been investigated for use in the treatment of hemorrhoids in a mixture with troxerutin. Carbazochrome interacts with α-adrenoreceptors on surface of platelets, which are coupled to Gq protein and initiate PLC IP3/DAG pathway to increase intracellular free calcium concentration with these subsequent actions: Activates PLA2 and induce arachidonic acid pathway to synthese endoperoxides (TxA2, thromboxane A2); Calcium binds to calmodulin which then binds and activates myosin light-chain kinase, that will enable the myosin crossbridge to bind to the actin filament and allow contraction to begin. This will change platelet’s shape and induce release of serotonin, ADP, vWF (Von Willebrand factor), PAF (Platelet-activating factor) to promote further aggregation and adhesion. Carbazochrome is usually used to treat bleeding tendency (for example purpura, etc.) caused by attenuation of microvascular resistance, bleeding from skin or mucosa and inner membrane, fundal/renal/uterine bleeding and intraoperative or postoperative abnormal bleeding.

Originator

Curator's Comment: On Monday, January 05, 1953, a U.S. federal trademark registration was filed for ADRENOSEM (Carbazochrome Sulfonic Acid) by BEECHAM INC., Bristol.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Phosphoinositide hydrolysis
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Preventing
ADONA

Approved Use

Hemorrhagic tendency (purpura etc.) due to decreased capillary resistance and increased capillary permeability. Hemorrhage from skin, mucous membrane and internal membrane, hemorrhage at eyeground, nephrotic hemorrhage and metrorrhagia. Abnormal bleeding during and after operation due to decrease of capillary resistance.

Launch Date

1955
Preventing
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
19.4 ng/mL
90 mg single, oral
dose: 90 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBAZOCHROME plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
77.94 ng × h/mL
90 mg single, oral
dose: 90 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBAZOCHROME plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.64 h
90 mg single, oral
dose: 90 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBAZOCHROME plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
PubMed

PubMed

TitleDatePubMed
Effect of carbazochrome sodium sulfonate on refractory chronic prostatitis.
2014-11
Optimization of solid phase extraction clean up and validation of quantitative determination of carbazochrome sodium sulfonate in human plasma by liquid chromatography-electrospray ionization tandem mass spectrometry.
2014-03-01
High-dose tranilast administration to rats creates interstitial cystitis-like symptoms with increased vascular permeability.
2013-11-26
Acute neurogenic pulmonary edema following electroconvulsive therapy: a case report.
2011-10-28
The ineffectiveness of carbazochrome salicylate (adrenosem) in the reduction of surgical bleeding.
1959-07
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Can also be injected intramuscularly, subcutaneously and intravenously http://drugs-infos.blogspot.ru/2009/08/adona.html
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:24:09 GMT 2025
Edited
by admin
on Wed Apr 02 09:24:09 GMT 2025
Record UNII
81F061RQS4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ADRENOCHROME MONOSEMICARBAZONE
MI  
Preferred Name English
CARBAZOCHROME
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
NSC-73742
Code English
CARBAZOCHROME [MART.]
Common Name English
ADRENOCHROME SEMICARBAZONE
Common Name English
3-HYDROXY-1-METHYL-5,6-INDOLINEDIONE SEMICARBAZONE
Systematic Name English
Carbazochrome [WHO-DD]
Common Name English
carbazochrome [INN]
Common Name English
CARBAZOCHROME [JAN]
Common Name English
ADRENOCHROME MONOSEMICARBAZONE [MI]
Common Name English
CARBAZOCHROME [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C78311
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
WHO-VATC QB02BX02
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
WHO-ATC B02BX02
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
Code System Code Type Description
MERCK INDEX
m1431
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL2051960
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
MERCK INDEX
m3059
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C79939
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
MESH
C073338
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
NSC
73742
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
RXCUI
2011
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY RxNorm
ECHA (EC/EINECS)
200-717-0
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
DRUG CENTRAL
491
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
INN
210
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
WIKIPEDIA
CARBAZOCHROME
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
CAS
69-81-8
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
DRUG BANK
DB09012
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
DAILYMED
81F061RQS4
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
PUBCHEM
5360410
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
SMS_ID
100000076277
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
EPA CompTox
DTXSID3048310
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
EVMPD
SUB13237MIG
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
FDA UNII
81F061RQS4
Created by admin on Wed Apr 02 09:24:09 GMT 2025 , Edited by admin on Wed Apr 02 09:24:09 GMT 2025
PRIMARY
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ACTIVE MOIETY