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Aphidicolin

Aphidicolin structure

CAS No:
38966-21-1
Formula:
C20H34O4
Chemical Name:
Aphidicolin
Synonyms:
8,11a-Methano-11aH-cyclohepta[a]naphthalene-4,9-dimethanol,tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-,(3R,4R,4aR,6aS,8R,9R,11aS,11bS)-;9,15-Cyclo-C,18-dinor-14,15-secoandrostane-4,17-dimethanol,3,17-dihydroxy-4-methyl-,(3α,4α,5α,17α)-;(3R,4R,4aR,6aS,8R,9R,11aS,11bS)-Tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-8,11a-methano-11aH-cyclohepta[a]naphthalene-4,9-dimethanol;8,11a-Methano-11aH-cyclohepta[a]naphthalene-4,9-dimethanol,tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-,[3R-(3α,4α,4aα,6aβ,8β,9β,11aβ,11bβ)]-;Aphidicolin;ICI 69653;NSC 234714;(+)-Aphidicolin;53334-90-0
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Aphidicolin is an inhibitor of DNA polymerase α and δ, prevents mitotic cell division by interfering with the activity of DNA polymerase[1].Aphidicolin is an antibiotic produced by the mold Cephalosporium aphidicola. Aphidicolin is a potent inhibitor of cellular deoxyribonucleic acid synthesis and inhibits the growth of herpes simplex virus[2].Aphidicolin potentiates apoptosis induced by arabinosyl nucleosides in a human promyelocytic leukemia cell line[3].

Aphidicolin is a tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. It has a role as an antimicrobial agent, an antiviral drug, an antineoplastic agent, an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor, a DNA synthesis inhibitor, an apoptosis inducer, a fungal metabolite, an Aspergillus metabolite and an antimitotic.|An antiviral antibiotic produced by Cephalosporium aphidicola and other fungi. It inhibits the growth of eukaryotic cells and certain animal viruses by selectively inhibiting the cellular replication of DNA polymerase II or the viral-induced DNA polymerases. The drug may be useful for controlling excessive cell proliferation in patients with cancer, psoriasis or other dermatitis with little or no adverse effect upon non-multiplying cells.

Aphidicolin Basic Attributes

Molecular Weight：

338.48

Exact Mass：

338.48

EC Number：

200-664-3

UNII：

192TJ6PP19

DSSTox ID：

DTXSID5036711

HScode：

29419090

Characteristics

PSA：

80.9

XLogP3：

1.69

Appearance：

colorless

Density：

1.2±0.1 g/cm3

Melting Point：

227-233 °C @ Solvent: Ethyl acetate

Boiling Point：

507.8±50.0 °C at 760 mmHg

Flash Point：

87℃

Refractive Index：

1.586

Water Solubility：

soluble in DMSO or methanol. Insoluble in water. Store solutions at -20°;ethanol: soluble 1mg/mL (stable at least a week at 4°C.)

Storage Conditions：

2-8°C

Vapor Pressure：

0.55 hPa ( 20 °C)

Specific rotation：

D27 +12° (c = 1 in methanol)

Safety Information

Transport codes：

NA 1993 / PGIII

wgk germany：

safety instructions：

22-24

RTECS Number：

PB9185000

Precautionary statement(s)：

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H315

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Drug Information

MeSH：

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

MeSH Entry Terms：

Aphidicolin

Aphidicolin Use and Manufacturing

Aphidicolin is a tetracyclic diterpene antibiotic isolated from fungi, notably Cephalosporium, Nigrospora, Harziella and Phoma. Aphidicolin has antibiotic, antiviral and antimitotic properties, blocking the cell cycle at early S-phase. This property has been used to synchronise cell division and is useful as a tool in cell differentiation research. Aphidicolin is a reversible inhibitor of DNA replication by inhibiting selected DNA polymerases. Aphidicolin induces apoptosis, prolongs the half-life of DNA methyltransferase, is active against Leishmania parasites and acts synergistically with the antitumor agents, vincristine and doxorubicin.

Computed Properties

Molecular Weight:338.5
XLogP3:2.5
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:338.24570956
Monoisotopic Mass:338.24570956
Topological Polar Surface Area:80.9
Heavy Atom Count:24
Complexity:524
Defined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of Aphidicolin

Shaanxi Dideu Medichem Co. Ltd Contact Supplier

CN
5 YRS

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APHIDICOLIN.

CAS No.: 38966-21-1

Grade: Pharmaceutical Grade

Content: 99%

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