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Details

Stereochemistry RACEMIC
Molecular Formula C10H11N4O5S.Na
Molecular Weight 322.273
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CARBAZOCHROME SODIUM SULFONATE

SMILES

[Na+].CN1C(CC2=C\C(=N\NC(N)=O)C(=O)C=C12)S([O-])(=O)=O

InChI

InChIKey=HLFCZZKCHVSOAP-DAMYXMBDSA-M
InChI=1S/C10H12N4O5S.Na/c1-14-7-4-8(15)6(12-13-10(11)16)2-5(7)3-9(14)20(17,18)19;/h2,4,9H,3H2,1H3,(H3,11,13,16)(H,17,18,19);/q;+1/p-1/b12-6-;

HIDE SMILES / InChI

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
Name Type Language
ADENARON
Preferred Name English
CARBAZOCHROME SODIUM SULFONATE
INN   MI   WHO-DD  
INN  
Official Name English
DONASEVEN
Brand Name English
ADRENOCHROME SEMICARBAZONE SODIUM SULFONATE
Common Name English
ADONA
Brand Name English
AC 17
Code English
TAZIN
Brand Name English
Carbazochrome sodium sulfonate [WHO-DD]
Common Name English
EMEX
Brand Name English
CARBAZON
Brand Name English
1H-INDOLE-2-SULFONIC ACID, 5-((AMINOCARBONYL)HYDRAZONO)-2,3,5,6-TETRAHYDRO-1-METHYL-6-OXO-, MONOSODIUM SALT
Common Name English
CARBAZOCHROME SODIUM SULPHONATE
Common Name English
1H-INDOLE-2-SULFONIC ACID, 5-(2-(AMINOCARBONYL)HYDRAZINYLIDENE)-2,3,5,6-TETRAHYDRO-1-METHYL-6-OXO-, SODIUM SALT (1:1)
Common Name English
AUZEI
Brand Name English
carbazochrome sodium sulfonate [INN]
Common Name English
ODANON
Brand Name English
AC-17
Code English
SODIUM SALT OF 5,6-DIHYDRO-1-METHYL-5,6-DIOXO-3-INDOLINE SULFONIC ACID 5-SEMICARBAZONE
Common Name English
2-INDOLINESULFONIC ACID, 5,6-DIHYDRO-1-METHYL-5,6-DIOXO-, 5-SEMICARBAZONE, SODIUM SALT
Common Name English
CARBAZOCHROME SODIUM SULFONATE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C78311
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
Code System Code Type Description
RXCUI
20209
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY RxNorm
SMS_ID
100000081337
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PRIMARY
INN
846
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PRIMARY
EVMPD
SUB06120MIG
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY
ECHA (EC/EINECS)
257-217-0
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PRIMARY
MERCK INDEX
m3060
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY Merck Index
FDA UNII
J0I08M946E
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PRIMARY
NCI_THESAURUS
C83589
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PRIMARY
EPA CompTox
DTXSID9022732
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PRIMARY
CAS
51460-26-5
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PRIMARY
ChEMBL
CHEMBL1697827
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PRIMARY
EVMPD
SUB13237MIG
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY