Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Carbazochrome
- DrugBank Accession Number
- DB09012
- Background
Carbazochrome is a hemostatic agent that promotes clotting, preventing blood loss from open wounds. It is an oxidation product of adrenaline which enhances the microcirculatory tone 4. In the future this may prevent excessive blood flow during surgical operations and the treatment of hemorrhoids, but research on effectiveness and severity of side effects remains inconclusive. It is not FDA-approved but is available as tablets or IM/SC injections in the treatment of hemorrhages in a number of countries.
Carbazochrome has been investigated for use in the treatment of non-surgical acute uncomplicated hemorrhoids in a mixture with Troxerutin, and this combination therapy demonstrated efficacy and safe tolerability either at a local or systemic level 1.
- Type
- Small Molecule
- Groups
- Experimental, Withdrawn
- Structure
Structure for Carbazochrome (DB09012)
- Weight
- Average: 236.231
Monoisotopic: 236.090940262 - Chemical Formula
- C10H12N4O3
- Synonyms
- 3-Hydroxy-1-methyl-5,6-inodlindionsemicarbazon
- Adchnon
- Adedolon
- Adrenostan
- Carbazochrom
- Carbazochrome
- Carbazochromum
- Carbazocromo
- External IDs
- EINECS 200-717-0
- NSC 73742
Pharmacology
- Indication
Indicated for capillary and parenchymal hemorrhage (trauma, tonsillectomy, during surgery), intestinal bleeding, and thrombocytopenic purpura.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Venous insufficiency Combination Product in combination with: Troxerutin (DB13124) •••••••••••• ••••••••• Used in combination for symptomatic treatment of Venous insufficiency Combination Product in combination with: Troxerutin (DB13124) •••••••••••• ••••••• •••••• - Contraindications & Blackbox Warnings
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Carbazochrome is an anti-bleeding agent that increases platelet aggregation and forms a platelet plug by interacting with α-adrenoreceptors on surface of platelets 5. It is shown to improve the structure of local capillary vessels in haemorrhage caused by fragility of capillaries. Carbazochrome capillary stabilizer that reverses pulmonary vascular hyperpermeability and decreases arterial PaO2 in experimental models 3.
- Mechanism of action
Carbazochrome interacts with platelet surface α-adrenoreceptors which are Gq-coupled receptors that leads to activation of PLC IP3/DAG pathway and increase in intracellular calcium levels. Elevated calcium ions bind to calmodulin and activates Ca2+/calmodulin-dependent myosin light chain kinase, allowing the myosin crossbridge to bind to the actin filament and polymerisation of globular actin (G-actin) to filamentous actin (F-actin) 2. Subsequent contraction of endothelial cells changes the shape of platelets and promotes the release of factors such as serotonin, ADP, Von Willebrand and platelet activating factor by platelets that induce aggregation and platelet adherence 5. Carbazochrome is reported to inhibit vascular hyperpermeability by inhibiting agonist-induced phosphoinositides hydrolysis caused by various vasoactive agents such as tryptase, thrombin and bradykinin 2.
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Adcar AC (Nisshin Pharmaceutical) / Adona (Tanabe) / Adonamin (Towa Yakuhin) / Adrenochrome (Quality Pharm) / Adrenoxil (Climax,) / Adrome (Landson) / Almetex (Alkaloid) / Anaroxyl (Organon) / Auzei (Nichi-Iko Pharmaceutical) / Carbajust (Yoshindo) / Chichina (Fuso Pharmaceutical) / Chromazol (Solas) / Crome (Ferron) / Cromin's (Infarmasa) / Di Ka Ning (Bosen Bio Pharmaceutical) / Fleboside (Acarpia-P) / Fleboton (Minapharm) / Ge Dan (Changfu Jiejing Pharmaceutical) / Hemosin K (Hormona) / Le Ka Ning (Pude) / Le Zhi Na (Tai'an Pharmaceutical Factory) / Luoye (Suzhou No.6) / Na Neng (Double-Crane) / Odanon (Towa Yakuhin) / Ophthalm K (Alfresa Pharma) / Ranobi (Koa Isei) / Styptochrome (Dr. Reddy's) / Su Bo Te (Laien Pharmaceutical) / Tai Si Neng (Tide Pharmaceutical) / Toxivenol (Kleva) / Velchrome (Novell Pharmaceutical) / Xue Yi Ting (Weifang Pharmaceutical Factory)
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Igatan F Carbazochrome (2 mg/1) + Ascorbic acid (156 mg/1) + alpha-Tocopherol acetate (10 mg/1) Capsule Oral OASIS TRADING 2018-11-20 Not applicable US 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Igatan F Carbazochrome (2 mg/1) + Ascorbic acid (156 mg/1) + alpha-Tocopherol acetate (10 mg/1) Capsule Oral OASIS TRADING 2018-11-20 Not applicable US
Categories
- ATC Codes
- B02BX02 — Carbazochrome
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Indoles and derivatives
- Sub Class
- Not Available
- Direct Parent
- Indoles and derivatives
- Alternative Parents
- Semicarbazones / N-alkylpyrrolidines / Vinylogous amides / Trialkylamines / Secondary alcohols / Organic carbonic acids and derivatives / Cyclic ketones / Enamines / Azacyclic compounds / Organopnictogen compounds show 2 more
- Substituents
- Alcohol / Aliphatic heteropolycyclic compound / Amine / Azacycle / Carbonic acid derivative / Carbonyl group / Cyclic ketone / Enamine / Hydrocarbon derivative / Indole or derivatives show 15 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 81F061RQS4
- CAS number
- 69-81-8
- InChI Key
- XSXCZNVKFKNLPR-SDQBBNPISA-N
- 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-
- IUPAC Name
- {[(5Z)-3-hydroxy-1-methyl-6-oxo-2,3,5,6-tetrahydro-1H-indol-5-ylidene]amino}urea
- SMILES
- CN1CC(O)C2=C\C(=N\NC(N)=O)C(=O)C=C12
References
- General References
- Squadrito F, Altavilla D, Oliaro Bosso S: Double-blind, randomized clinical trial of troxerutin-carbazochrome in patients with hemorrhoids. Eur Rev Med Pharmacol Sci. 2000 Jan-Apr;4(1-2):21-4. [Article]
- Sendo T, Itoh Y, Aki K, Oka M, Oishi R: Carbazochrome sodium sulfonate (AC-17) reverses endothelial barrier dysfunction through inhibition of phosphatidylinositol hydrolysis in cultured porcine endothelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2003 Sep;368(3):175-80. Epub 2003 Aug 20. [Article]
- Sendo T, Goromaru T, Aki K, Sakai N, Itoh Y, Oishi R: Carbazochrome attenuates pulmonary dysfunction induced by a radiographic contrast medium in rats. Eur J Pharmacol. 2002 Aug 23;450(2):203-8. [Article]
- Basile M, Gidaro S, Pacella M, Biffignandi PM, Gidaro GS: Parenteral troxerutin and carbazochrome combination in the treatment of post-hemorrhoidectomy status: a randomized, double-blind, placebo-controlled, phase IV study. Curr Med Res Opin. 2001;17(4):256-61. [Article]
- Ghareeb H, Karaman R. (2015). 6. In Commonly Used Drugs: Uses, Side Effects, Bioavailability and Approaches to Improve It (1st ed., pp. 210). Nova Science Pub Inc; UK ed. edition. [ISBN:9781634638289 ]
- External Links
- KEGG Drug
- D01864
- PubChem Compound
- 5360410
- PubChem Substance
- 310264970
- ChemSpider
- 4514501
- 2011
- ChEMBL
- CHEMBL2051960
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Carbazochrome
- MSDS
- Download (47.4 KB)
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intramuscular Tablet, coated Oral Capsule Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.91 mg/mL ALOGPS logP -0.47 ALOGPS logP -1.2 Chemaxon logS -1.9 ALOGPS pKa (Strongest Acidic) 11.64 Chemaxon pKa (Strongest Basic) 1.98 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 108.02 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 62.16 m3·mol-1 Chemaxon Polarizability 23.09 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0190000000-6e3203737418fed8d203 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0900000000-34bcd55df786bea8c32a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-022c-0900000000-3c9e282e2b5936a70871 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0910000000-b4f8b88bea3107e423fc Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a6r-1900000000-fd92dae3bff015d12603 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9800000000-3330b5d73db0dd43d244 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 152.77473 predictedDeepCCS 1.0 (2019) [M+H]+ 155.13274 predictedDeepCCS 1.0 (2019) [M+Na]+ 161.22588 predictedDeepCCS 1.0 (2019)
Drug created at June 20, 2014 21:49 / Updated at February 21, 2021 18:52