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...

基本信息

化学结构

分子式

C₁₇H₁₇ClO₆

分子量

352.76628

精确质量

352.07136594

电荷

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

计算属性

JChem

Acid pKa

17.688671

质子受体

质子供体

LogD (pH = 5.5)

2.1721375

LogD (pH = 7.4)

2.1721375

Log P

2.1721375

摩尔折射率

87.8459

极化性

33.75892

极化表面积

71.06

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

2.71

LOG S

-3.84

溶解度

5.04e-02 g/l

数据来源

名称和标识

别名

(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标准名

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

IUPAC传统名

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

商标名

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

名称和标识

数据登录号

MDL号

MFCD00082343

PubChem SID

24895099160963746248698932489518546508437

CAS号

EC号

Beilstein号

PubChem CID

ATC码

CHEMBL

Medline Plus

DrugBank ID

美国药典/FDA物质标识码

维基百科标题

CHEBI ID

KEGG ID

Chemspider ID

默克索引号

数据登录号

化合物性质

药理学性质

半衰期

9-21 hours

法定药品分级

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

给药途径

Oral

生物利用度

Highly variable (25 to 70%)

代谢

Hepatic demethylation and glucuronidation

妊娠期药物分类

B3 (Australia), C (United States)

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

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

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
抗有丝分裂。

46309

法律信息
VETRANAL 商标 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.

描述信息

参考文献

PubChem文献

数据源提供

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

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

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

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

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

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

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

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

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

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

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

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

• 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)

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

参考文献

生物活性

PubChem BioAssay

生物活性