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Details

Stereochemistry RACEMIC
Molecular Formula C10H12N4O5S
Molecular Weight 300.291
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CARBAZOCHROME SULFONIC ACID

SMILES

CN1C(CC2=C\C(=N\NC(N)=O)C(=O)C=C12)S(O)(=O)=O

InChI

InChIKey=OZCACMPSTYQSMM-SDQBBNPISA-N
InChI=1S/C10H12N4O5S/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)/b12-6-

HIDE SMILES / InChI

Molecular Formula C10H12N4O5S
Molecular Weight 300.291
Charge 0
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 Sat Dec 16 02:17:58 GMT 2023
Edited
by admin
on Sat Dec 16 02:17:58 GMT 2023
Record UNII
BMQ12812QR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBAZOCHROME SULFONIC ACID
Common Name English
1H-INDOLE-2-SULFONIC ACID, 5-((AMINOCARBONYL)HYDRAZONO)-2,3,5,6-TETRAHYDRO-1-METHYL-6-OXO-
Common Name English
2-INDOLINESULFONIC ACID, 5,6-DIHYDRO-1-METHYL-5,6-DIOXO-, 5-SEMICARBAZONE
Common Name English
1H-INDOLE-2-SULFONIC ACID, 5-(2-(AMINOCARBONYL)HYDRAZINYLIDENE)-2,3,5,6-TETRAHYDRO-1-METHYL-6-OXO-
Common Name English
ADRENOCHROME SEMICARBAZONE SULFONIC ACID
Common Name English
Code System Code Type Description
CAS
70063-04-6
Created by admin on Sat Dec 16 02:17:58 GMT 2023 , Edited by admin on Sat Dec 16 02:17:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID80860629
Created by admin on Sat Dec 16 02:17:58 GMT 2023 , Edited by admin on Sat Dec 16 02:17:58 GMT 2023
PRIMARY
PUBCHEM
6258971
Created by admin on Sat Dec 16 02:17:58 GMT 2023 , Edited by admin on Sat Dec 16 02:17:58 GMT 2023
PRIMARY
FDA UNII
BMQ12812QR
Created by admin on Sat Dec 16 02:17:58 GMT 2023 , Edited by admin on Sat Dec 16 02:17:58 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT