formycin A

Names

[ Name ]:
formycin A

[Synonym ]:
formycin
FORMYCIN A MONOHYDRATE
FORMYCIN MONOHYDRATE
7-AMINO-3-β-D-RIBOFURANOSYL-1H-PYRAZOLO[4,3-D]PYRIMIDINE MONOHYDRATE
8-AZA-9-DEAZAADENOSINE MONOHYDRATE

Biological Activity

[Description]:

Formycin A (NSC 102811), a purine nucleoside antibiotic, is a potent human immunodeficiency virus type 1 (HIV-1) inhibitor with an EC50 of 10 μM. Formycin A shows antitumor and antiviral activities[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

[Target]

HIV-1:10 μM (EC50)

[In Vitro]

Formycin A (NSC 102811; 1 μM, 5 μM, 10 μM) antagonizes Zidovudine (AZT; a dideoxynucleoside chain terminator).

[References]

[1]. Dapp MJ , et al. Discovery of novel ribonucleoside analogs with activity against human immunodeficiency virus type 1.J Virol. 2014 Jan;88(1):354-63.

[2]. Zhang M, et al. Comparative Investigation into Formycin A and Pyrazofurin A Biosynthesis Reveals Branch Pathways for the Construction of C-Nucleoside Scaffolds. Appl Environ Microbiol. 2020 Jan 7;86(2).

Chemical & Physical Properties

[ Density]:
1.771g/cm3

[ Boiling Point ]:
709.5ºC at 760 mmHg

[ Melting Point ]:
153-155ºC

[ Molecular Formula ]:
C₁₀H₁₃N₅O₄

[ Molecular Weight ]:
285.25700

[ Flash Point ]:
382.9ºC

[ Exact Mass ]:
285.10700

[ PSA ]:
159.63000

[ Index of Refraction ]:
1.803

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UR0719000

CHEMICAL NAME :: 1H-Pyrazolo(4,3-d)pyrimidine, 7-amino-3-beta-D-ribofuranosyl-

CAS REGISTRY NUMBER :: 6742-12-7

LAST UPDATED :: 199612

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C10-H13-N5-O4

MOLECULAR WEIGHT :: 267.28

WISWESSER LINE NOTATION :: T56 BMN FN HNJ IZ D- BT5OTJ CQ DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Blood - hemorrhage Blood - changes in spleen Blood - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 125 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 165 mg/kg/5D-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 mg/kg/8D-I

TOXIC EFFECTS :: Related to Chronic Data - death

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - mouse Leukocyte

DOSE/DURATION :: 25700 ug/L

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 30,481,1987

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
UR0719000

Articles

Purine nucleoside metabolism in the erythrocytes of patients with adenosine deaminase deficiency and severe combined immunodeficiency.

J. Clin. Invest. 57(4) , 1025-35, (1976)

Deficiency of erythrocytic and lymphocytic adenosine deaminase (ADA) occurs in some patients with severe combined immunodeficiency disease (SCID). SCID with ADA deficiency is inherited as an autosomal...

The riddle of formycin A insulinotropic action.

Biochem. Mol. Med. 57(1) , 47-63, (1996)

Formycin A augments insulin release evoked by glucose (5.6 mm or more), this effect not being rapidly reversible. The mechanism responsible for the insulinotropic action of formycin A was investigated...

Tautomerism of the nucleoside antibiotic formycin, as studied by carbon-13 nuclear magnetic resonance.

J. Am. Chem. Soc. 95(14) , 4761-2, (1973)