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Details

Stereochemistry RACEMIC
Molecular Formula C10H13N5O2.CH4O3S
Molecular Weight 331.348
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ADRENOCHROME MONOAMINOGUANIDINE MESILATE ANHYDROUS

SMILES

CS(O)(=O)=O.CN1CC(O)C2=C\C(=N\NC(N)=N)C(=O)C=C12

InChI

InChIKey=IGWUYHOAVVECKR-FJMCHERXSA-N
InChI=1S/C10H13N5O2.CH4O3S/c1-15-4-9(17)5-2-6(13-14-10(11)12)8(16)3-7(5)15;1-5(2,3)4/h2-3,9,17H,4H2,1H3,(H4,11,12,14);1H3,(H,2,3,4)/b13-6-;

HIDE SMILES / InChI
Adrenochrome monoaminoguanidine (S-Adchnon) is a hemostatic capillary-stabilizing agent demonstrating pharmacological effects against radiation injury by reducing side effects of radiation therapy on hematopoietic organ. Synthesized by a dehydrating reaction of adrenochrome and aminoguanidine it has superior properties than adrenochrome, an oxidation product of adrenalin remarkable for its efficiency as a haemostatic agent at very small doses and for its more rapid and equally intense action than that of adrenalin. Adrenochrome does not alter the cardiac rhythm and does not cause any hypertension or internal haemorrhages and would be suitable for therapeutic applications, however, its instability, in aqueous or alcoholic solution, makes its use substantially impossible. S-Adchnon was devised, approved by the Japanese Ministry of Health, Labor and Welfare in 1962 and used widely in Japan. Adrenochrome monoaminoguanidine has negligible toxicity, stable and could be made into salts for aqueous dosage, especially for injection. Adrenochrome monoaminoguanidine methanesulfonate (AMM) enhances the recovery from radiation-induced leukopenia in rabbits and in humans, and inhibits the increases in chromosome aberrations in peripheral lymphocytes of patients with cervical carcinoma under radiotherapy. It has been shown that the radiation-induced initial decrease in number of peripheral blood leukocytes (PBL) is not affected by AMM, but recovery from the decrease is enhanced, shortening the period of leukopenia. This suggests that AMM may not exert its effects by protecting PBL directly but by protecting stem and/or progenitor cells in hematogenesis which proliferate and differentiate to PBL after irradiation. In in vitro colony formation method AMM demonstrated a protective effect on the survival of GM-CFC, a hematopoietic progenitor cells. Differential action on cancer and normal tissue by AMM and cytochrome C combined with radiotherapy was demonstrated. AMM in combination with cytochrome C augumented natural killer (NK) cells activity in KSN nude mice, protected potent NK cells in patients with lung cancer against radiotherapy and sensitized the human lung cancer xenografts to radiotherapy. Thus, AMM and cytochrome C may have the potential as a differential modulator of radiosensitivity of normal tissues and of tumors.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
S-Adchnon

Approved Use

Approved for use as a hemostatic capillary-stabilizing agent by Japanese Ministry of Health, Labor and Welfare

Launch Date

1962
PubMed

PubMed

TitleDatePubMed
Protective effect of adrenochrome monoguanylhydrozone methansulfonate (S-Adchnon) on the hematopoietic organ as revealed in irradiated cancer patients.
1971 Jun
[Evaluation of radiation-protective effect of S-adchnon].
1974 Nov
Radioprotective effects of adrenochrome monoaminoguanidine methanesulfonate (AMM) on irradiated C57BL mice and the survival of GM-CFC, a hematopoietic progenitor cell.
1988 Dec
[Effect of cepharanthin on radiotherapy induced leukopenia].
1990 Apr
Differential action on cancer and normal tissue by adrenochrome monoaminoguanidine methanesulfonate and cytochrome C combined with radiotherapy.
1994 Jun 15
Effects of combination of immunomodulators and an adrenochrome derivative on survival of irradiated mice.
1994 Jun 15
[A 50-year history of new drugs in Japan-the development and trends of hemostatics and antithrombotic drugs].
2003
Patents

Patents

Sample Use Guides

100-300 mg of S-Adchnon (adrenochrome monoguanylhydrozone methansulfonate) was given 15-30 minutes before every expected irradiation by single intravenous injection, or it was administered in divided doses orally during the course of radiation therapy of cancer patients.
Route of Administration: Intravenous
In Vitro Use Guide
Isolated bone marrow cells from C57BL mice were incubated for 30 min before and 4 hr after irradiation with 25 and 100 ug/ml adrenochrome monoaminoguanidine methanesulfonate (AMM).
Name Type Language
ADRENOCHROME MONOAMINOGUANIDINE MESILATE ANHYDROUS
Common Name English
5,6-INDOLEDIONE, 3-HYDROXY-1-METHYL-, 5-(AMIDINOHYDRAZONE), MONOMETHANESULFONATE (SALT)
Common Name English
ADRENOCHROME GUANYLHYDRAZONE MESILATE
WHO-DD  
Common Name English
S-ADCHNONE
Common Name English
ADRENOCHROME MONOAMINOGUANIDINE MESILATE
Common Name English
GUANIDINE, ((5,6-DIHYDRO-3-HYDROXY-1-METHYL-6-OXO-5- INDOLINYLIDENE)AMINO)-, MONOMETHANESULFONATE (SALT)
Common Name English
DIAZENECARBOXIMIDAMIDE, 2-(2,3,5,6-TETRAHYDRO-3-HYDROXY-1-METHYL-6-OXO-1H-INDOL-5-YL)-, METHANESULFONATE (1:1)
Systematic Name English
S-ADCHNON
Common Name English
Adrenochrome guanylhydrazone mesilate [WHO-DD]
Common Name English
ADRENOCHROME GUANYLHYDRAZONE MESYLATE
Common Name English
HYDRAZINECARBOXIMIDAMIDE, 2-(1,2,3,6-TETRAHYDRO-3-HYDROXY-1- METHYL-6-OXO-5H-INDOL-5-YLIDENE)-, MONOMETHANESULFONATE (SALT)
Common Name English
ADRENOCHROME MONOGUANYLHYDRAZONE METHANESULFONATE
Common Name English
METHANESULFONIC ACID, COMPD. WITH (3-HYDROXY-1-METHYL-6-OXO- 5(6H)-INDOLINYLENEAMINO)GUANIDINE
Common Name English
ADCHNON S
Common Name English
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