CAS 126-07-8|(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione|(2S)-trans-7-Chloro-2′,4,6-trimethoxy-6′-methylspiro(benzofuran-2[3H],1′-[2]cyc...

General Information

Structure

Molecular Formula

C₁₇H₁₇ClO₆

Molecular Mass

352.76628

Exact Mass

352.07136594

Charge

InChI

InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1

InChIKey

DDUHZTYCFQRHIY-RBHXEPJQSA-N

Canonic Smiles

COC1=CC(=O)C[C@H]([C@@]21Oc1c(C2=O)c(OC)cc(c1Cl)OC)C

Isomeric Smiles

Clc1c2O[C@]3([C@@H](CC(=O)C=C3OC)C)C(=O)c2c(OC)cc1OC

Calculated Properties

JChem

Acid pKa

17.688671

H Acceptors

H Donor

LogD (pH = 5.5)

2.1721375

LogD (pH = 7.4)

2.1721375

Log P

2.1721375

Molar Refractivity

87.8459

Polarizability

33.75892

Polar Surface Area

71.06

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

2.71

LOG S

-3.84

Solubility (Water)

5.04e-02 g/l

Data Source

Names and Identifiers

Synonyms

(2S)-trans-7-Chloro-2′,4,6-trimethoxy-6′-methylspiro(benzofuran-2[3H],1′-[2]cyclohexene)-3,4′-dioneGriseofulvin灰黄霉素(1'S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohex[2]ene]-3,4'-dione(+)-GriseofulvinGriseofulvin(+)-灰黄霉素灰黄霉素(2S)-反式-7-氯-2′,4,6-三甲氧基-6′-甲基螺(苯并呋喃-2[3H],1′-[2]环己烯)-3,4′-二酮GriseofulvinGriseofulvina [INN-Spanish]Griseofulvinum [INN-Latin]Griseofulvine [INN-French](2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dioneGrisactinIdifulvinNorofulvinFulcinGrisovinAmudaneLikudenGrifulvinGricinFulvicinCurling factorGrisoviSporostatin(+)-GriseofulvinXuanjing(1'S,6'R)-7-Chloro-2',4,6-trimethoxy-6'-methyl-spiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dioneSpirofulvin

IUPAC name

(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

IUPAC Traditional name

griseofulvin (2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

Brand Name

Gris-PEGFulvicin U/FGrisetinFulvinilLikudenGriseoGrysioGricinLamorylDelmofulvinaSpirofulvinGrifulvinNeo-FulcinFulvicin-P/GGrizeofulvinGriseofulvin forteFulvicin-U/FFulvicinBiogrisin-fpLikundenGriseofulvin-forteXuanjingGriseomixGresfeedFungivinPoncylGrifulvin VSporostatin xanFulcinGrisovin FPGrisactinGrisofulvinGrisovinCurling factorFulvican grisactinMurfulvinGrifulinGrisactin UltraNeocidGrisefulineGuservinAmudaneFulvistatinGriscofulvinFulcineGreosinFulvicin P/GFulvinaSporostatin

Names and Identifiers

Registration numbers

MDL Number

MFCD00082343

PubChem SID

24895099160963746248698932489518546508437

EC Number

CAS Number

Beilstein Number

PubChem CID

ATC CODE

CHEMBL

DrugBank ID

Medline Plus

Wikipedia Title

Unique Ingredient Identifier

CHEBI ID

Chemspider ID

KEGG ID

Merck Index

Registration numbers

Properties

Pharmacology Properties

Half Life

9-21 hours

Legal Status

POM (UK), ?-only (U.S.)

Admin Routes

Oral

Bioavailability

Highly variable (25 to 70%)

Metabolism

Hepatic demethylation and glucuronidation

Pregnancy Category

B3 (Australia), C (United States)

Binds tightly to new keratin which becomes highly resistant to fungal invasions

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00400

Drug Groups

approved

Description

An antifungal antibiotic. Griseofulvin may be given by mouth in the treatment of tinea infections. [PubChem]

Indication

For the treatment of ringworm infections of the skin, hair, and nails, namely: tinea corporis, tinea pedis, tinea cruris, tinea barbae, cradle cap or other conditions caused by Trichophyton or Microsporum fungi.

Pharmacology

Griseofulvin is a mycotoxic metabolic product of Penicillium spp. It was the first available oral agent for the treatment of dermatophytoses and has now been used for more than forty years. Griseofulvin is fungistatic with in vitro activity against various species of Microsporum Epidermophyton, and Trichophyton. It has no effect on bacteria or on other genera of fungi. Following oral administration, griseofulvin is deposited in the keratin precursor cells and has a greater affinity for diseased tissue. The drug is tightly bound to the new keratin which becomes highly resistant to fungal invasions. Once the keratin-Griseofulvin complex reaches the skin site of action, it binds to fungal microtubules (tubulin) thus altering fungal mitosis.

Toxicity

Side effects are minor: headaches, gastrointestinal reactions and cutaneous eruptions

Affected Organisms

Yeast and other Trichophyton or Microsporum fungi

Biotransformation

Primarily hepatic with major metabolites being 6-methyl-griseofulvin and its glucuronide conjugate.

Absorption

Poorly absorbed from GI ranging from 25 to 70% of an oral dose. Absorption is significantly enhanced by administration with or after a fatty meal.

Half Life

9-21 hours

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Wikipedia

Griseofulvin

Sigma Aldrich

G2664

Biochem/physiol Actions
Griseofulvin disrupts microtubule assembly and mitotic spindle stucture possibly via tubulin aggregation.

G4753

Biochem/physiol Actions
Antifungal. Mode of action: Disrupts the mitotic spindle structure and inhibits nuclear division.1 Induces apoptosis in human tumor cell lines.2
包装
5, 25, 50 g in poly bottle

856444

Features and Benefits
Antimitotic.

46309

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

TRC

G787500

It is an antifungal drug. It is used both in animal and in humans, to treat rigworm infections of the skin and nails. It is derived from the mold Penicillium griseofulvum.

Molecule Details

References

PubChem Literature

From Data Sources

• Townley, E.R., et al.: Anal. Profiles Drug Subs., 8, 219 (1939)

• Oxford, et al.: Biochem. J., 33, 240 (1939)

• Stork, G. et al., J.A.C.S., 1962, 84, 310; 1964, 86, 471, (synth, ir, uv, nmr)

• Walker, F.J., Diss. Abstr. Int., B, 1982, 42, 4801, (synth)

• Brown, W.A.C. et al., J.C.S., 1963, 1050, (cryst struct)

• Malmros, G. et al., Cryst. Struct. Commun., 1977, 6, 463, (cryst struct)

• Hassan, M.A. et al., Anal. Profiles Drug Subst., 1980, 9, 583, (rev)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1309B, (nmr)

• IARC Monog., 1976, 10, 153; Suppl. 7, 391, (rev, tox)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, GKE000

• Takeuchi, Y. et al., Chem. Pharm. Bull., 1997, 45, 327; 2011-2015, (synth)

• Cole, R.J. et al., Handbook of Toxic Fungal Metabolites, Academic Press, New York, 1981, 857; 862

• Puttaraja, N.K.A. et al., J. Crystallogr. Spectrosc. Res., 1982, 12, 415, (cryst struct)

• Itai, A. et al., Chem. Pharm. Bull., 1985, 33, 158, (isomer)

• Levine, S.G. et al., Tet. Lett., 1971, 311, (pmr, conformn)

• Sato, Y. et al., Tet. Lett., 1976, 3971, (cmr, biosynth)

• Levine, S.G. et al., J.O.C., 1975, 40, 2540, (cmr)

• Pirrung, M.C. et al., J.A.C.S., 1991, 113, 8561, (synth)

• Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 3, 483, (rev)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 323

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 321D, (ir)

• McMaster, W.J. et al., J.C.S., 1960, 4628, (Dehydrogriseofulvin, Dechlorogriseofulvic acid)

• Oda, T. et al., Chem. Pharm. Bull., 1983, 31, 934, (synth, derivs)

• Tomozane, H. et al., Chem. Pharm. Bull., 1990, 38, 925, (synth, bibl)

• Grove, J.F. et al., J.C.S., 1952, 3949; 3967, (struct, abs config)

• Kingston, D.G.I. et al., Phytochemistry, 1976, 15, 1037, (deriv)

• Townley, E.R., Anal. Profiles Drug Subst., 1979, 8, 219, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 4313, (synonyms)

• Pesticide Manual, 9th edn., 1991, No. 6970

• Danishefsky, S. et al., J.A.C.S., 1979, 101, 7018, (synth)

• Hussain, S.A., Diss. Abstr. Int., B, 1986, 47, 2394

• MacMillan, J., J.C.S., 1953, 1697, (deriv)

• Davies, R.R., Antifungal Chemother., 1980, 149, (rev, pharmacol, tox)

• Takeuchi, Y. et al., Chem. Pharm. Bull., 1991, 39, 3045, (synth)

References

Bioactivity

PubChem BioAssay

Bioactivity