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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

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C10H11N4O5S
Molecular Weight 299.283
Charge -1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 1
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/13257997

Adrenochrome is one of the principal oxidation products of epinephrine and has no significant pressor action. It has been studied in Europe since 1937 and in America since 1951 for its action in control of bleeding from capillaries and venules. Its role seems independent of the chemistry of coagulation, the vitamin K-prothrombin mechanism, and the function of heparin or the usual anticoagulants. It is alleged to reduce capillary permeability and to increase capillary resistance. Both natural and synthetic adrenochrome are markedly unstable and insoluble. Evolution of the adrenochrome monosemicarbazone sodium salicylate complex has overcome these chemical difficulties. This product is synthetically prepared in America under the trade name Adrenosem and the generic name of carbazochrome. The loss of blood was measured in fifty-three patients who underwent multiple extractions and alveoloplasty under general anesthesia. No local anesthetic was employed in any case. Of the fifty-three patients, twenty-six were prepared preoperatively by the intramuscular injection of 5 mg of carbazochrome (Adrenosem) salicylate one and one-half to two hours prior to the operation. The remaining twenty-seven patients served as a control group. When operations of equal extent and severity were compared, it was found that no effective benefit in reduction of loss of blood at operation was noted in the patients treated with carbazochrome salicylate.

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
PubMed

PubMed

TitleDatePubMed
The ineffectiveness of carbazochrome salicylate (adrenosem) in the reduction of surgical bleeding.
1959 Jul
Acute neurogenic pulmonary edema following electroconvulsive therapy: a case report.
2012 Nov-Dec
High-dose tranilast administration to rats creates interstitial cystitis-like symptoms with increased vascular permeability.
2013 Nov 26
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 Mar 1
Effect of carbazochrome sodium sulfonate on refractory chronic prostatitis.
2014 Nov
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
In general, for adults, take 10 to 30mg of the active ingredient at a time 3 times a day. The dosage may be adjusted according to disease, age and symptoms of the patient. This preparation contains 30mg of the active ingredient in a tablet.
Route of Administration: Oral
In Vitro Use Guide
0.1-1 M of carbazochrome sulfonic acid reversed the barrier dysfunction induced by tryptase, thrombin and bradykinin in cultured porcine aortic endothelial cells.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:10:30 GMT 2023
Edited
by admin
on Fri Dec 15 16:10:30 GMT 2023
Record UNII
J0I08M946E
Record Status Validated (UNII)
Record Version
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Name Type Language
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
ADENARON
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C78311
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
Code System Code Type Description
RXCUI
20209
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
PRIMARY RxNorm
SMS_ID
100000081337
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
PRIMARY
INN
846
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
PRIMARY
EVMPD
SUB06120MIG
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
PRIMARY
ECHA (EC/EINECS)
257-217-0
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
PRIMARY
MERCK INDEX
m3060
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
PRIMARY Merck Index
FDA UNII
J0I08M946E
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
PRIMARY
NCI_THESAURUS
C83589
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID9022732
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
PRIMARY
CAS
51460-26-5
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
PRIMARY
ChEMBL
CHEMBL1697827
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
PRIMARY
EVMPD
SUB13237MIG
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY