Carbazochrome

Carbazochrome

Structural formula of carbazochrome
Space-filling model of the carbazochrome molecule
Systematic (IUPAC) name
[(3-Hydroxy-1-methyl-6-oxo-2,3-dihydroindol-5-ylidene)amino]urea
Clinical data
Trade names	Toxivenol
AHFS/Drugs.com	International Drug Names
Routes of administration	P/O, I/M
Identifiers
CAS Number	69-81-8
ATC code	B02BX02 (WHO)
PubChem	CID: 5360410
DrugBank	DB09012 Y
ChemSpider	4514501
UNII	81F061RQS4 Y
ChEMBL	CHEMBL2051960
Chemical data
Formula	C10H12N4O3
Molecular mass	236.23 g/mol
SMILES O=C(N)N/N=C1/C=C2\C(=C/C1=O)N(CC2O)C
InChI 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- Key:XSXCZNVKFKNLPR-SDQBBNPISA-N
(verify)

Carbazochrome 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.

With troxerutin, it has been investigated for use in the treatment of hemorrhoids.

Indications

Capillary and parenchymal hemorrhage (trauma, tonsillectomy, during surgery), intestinal bleeding, thrombocytopenic purpura.

Mechanism of action

Carbazochrome, the semicarbazone of adrenochrome, that 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.

Vector

Because of its poor solubility in water it must be first thoroughly dissolved in alcohol, melted fat (butter), or vegetable oil (to aid in absorption) and then ingested.