Griseofulvin

An orally administered antifungal antibiotic used to treat dermatophyte infections, particularly tinea capitis and selected infections of the skin and nails caused by Trichophyton, Microsporum, and Epidermophyton species. Griseofulvin disrupts fungal microtubule dynamics and mitotic spindle function, inhibiting fungal cell division. It accumulates in newly formed keratin, helping protect growing skin, hair, and nails from fungal invasion. It is ineffective against Candida infections and is often replaced by newer antifungal agents for certain indications

CAS Number: 126-07-8

Molecular Mass: 352.8 g/mol

Formula: C₁₇H₁₇ClO₆

Smiles: COC1=CC(=O)C[C@@H](C)[C@]12Oc1c(Cl)c(OC)cc(OC)c1C2=O

Synonymes:

Griseofulvin, griseofulvin, 126-07-8, (+)-Griseofulvin, Fulvicin, Amudane, Fulcin, Griseofulvina, Griseofulvinum, Grifulvin, Grisactin, Grisovin, Spirofulvin, Lamoryl, Curling factor, Grisefuline, Griseofulvine, Grisofulvin, Grizeofulvin, Likuden, Grysio, Poncyl, Neo-Fulcin, Delmofulvina, Fulvicin-P/G, Fulvinil, Fulvistatin, Fungivin, Gresfeed, Grifulin, Griscofulvin, Guservin, Murfulvin, Fulcine, Fulvina, Greosin, Biogrisin-FP, Fulvican grisactin, Griseofulvin-forte, Fulvicin-U/F, Xuanjing, Grisactin V, GRISEOFULVIN, MICROCRYSTALLINE, Gricin, Griseo, Grifulvin V, USAF SC-2, Griseofulvin microsize, NSC 34533, GRISEOFULVIN, MICROSIZE, NSC-755822, 32HRV3E3D5, (2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione, DTXSID8020674, Griseofulvin permeability diameter, NSC-34533, 7-Chloro-4,6,2'-trimethoxy-6'-methylgris-2'-en-3,4'-dione, DTXCID20674, (2S,5'R)-7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione, Spiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (1'S-trans)-, CHEBI:27779, 7-Chloro-2',4,6-trimethoxy-6'beta-methylspiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, (1'S,6'R)-7-Chloro-2',4,6-trimethoxy-6'-methylspiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, Spiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (2S-trans)-, FulvicinUF, GrisPEG, Fulvicin U F, Griseofulvin, (+)-, Gris PEG, Spiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (1'S,6'R)-, GRISEOFULVIN POWDER, Fulsovin, Grivate, Grisol af, (2S,5'R)-7-chloro-3',4,6-trimethoxy-5'-methylspiro(1-benzofuran-2,4'-cyclohex-2-ene)-1',3-dione, (2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro(1-benzofuran-2,1'-cyclohexan)-2'-ene-3,4'-dione, Grysio (Microsize), Fulvicin U/F Powder, Fulcin 125, Fulcin 500, Fulvicin U/F Tablets, RefChem:5870, Griseofulvin (microsize), Griseofulviin (microsize), Ultramicrosize Griseofulvin, Fulvicin U/F Bolus Veterinary, D01AA08, D01BA01, Ultramicrosize Griseofulvin Tablets, (1'S-trans)-7-Chloro-2',4,6-trimethoxy-6'-methylspiro(benzofuran-2(3H),1'-cyclohex-2'-ene)-3,4'-dione, 204-767-4, Griseofulvine [INN-French], Griseofulvinum [INN-Latin], Griseofulvina [INN-Spanish], Grisetin, MFCD00082343, GRISEOFULVIN, ULTRAMICROCRYSTALLINE, C17H17ClO6, Griseofulvin (Standard), Griseomix, Grisactin Ultra, Griseofulvin forte, Fulvicin P/G, NCGC00091120-01, (1'S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohex[2]ene]-3,4'-dione, (1'S-trans)- 7-Chloro-2',4,6-trimethoxy-6'-methylspiro(benzofuran-2(3H),1'-cyclohex-2'-ene)-3,4'-dione, (2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H,4'H-spiro[1-benzofuran-2,1'-cyclohex[2]ene]-3,4'-dione, ULTRAGRIS-165, ULTRAGRIS-330, Fulvicin Bolus, Fulvicin-U/F (Veterinary), Fulvicin Bolus (Veterinary), FULVICIN P/G 165, FULVICIN P/G 330, Caswell No. 471B, Fulvidex, (2S,5'R)-7-chloro-3',4,6-trimethoxy-5'-methyl-spiro[benzofuran-2,4'-cyclohex-2-ene]-1',3-dione, SMR000718755, CCRIS 320, HSDB 1722, SR-05000001535, 2884-22-2, EINECS 204-767-4, EPA Pesticide Chemical Code 471400, Griseofulvin and Alpha-IFN, BRN 0095226, UNII-32HRV3E3D5, Norofulvin, , AI3-51015, Grifulvin, , Grisactin, , Griseofulvin RS, Curling factor, , Fulvicin, , Grisovin, , Amudane, , fulvicin UF, Likuden, , Fulcin, , Gricin, , Griseofulvin [USP:INN:BAN:JAN], (+)-Epigriseofulvin, 7-Chloro-2',4,6-trimethoxy-6'alpha-methyl-spiro[benzofuran-2(3H)-1'-[2]cyclohexene]-3,4'-dione, (1'R,6'R)-7-Chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohex[2]ene]-3,4'-dione, Prestwick_247, Grisactin V (TN), Gris-peg (TN), IDIFULVIN, Griseofulvin,microsize, Spectrum_000816, CPD000718755, SpecPlus_000336, Prestwick3_000226, Spectrum2_000213, Spectrum3_000161, Spectrum4_000927, Spectrum5_000648, GRISEOFULVIN [MI], Griseofulvin [USP:INN], GRISEOFULVIN [INN], GRISEOFULVIN [JAN], CHEMBL562, GRISEOFULVIN [HSDB], GRISEOFULVIN [IARC], 7-Chloro-4,6-dimethoxycoumaran-3-one-2-spiro-1'-(2'-methoxy-6'-methylcyclohex-2'-en-4'-one), GRISEOFULVIN [VANDF], SCHEMBL21988, Amudane, Fulvicin, Grisactin, BSPBio_000271, BSPBio_001621, GRISEOFULVIN [MART.], KBioGR_001454, KBioSS_001296, SPECTRUM200046, (2S-trans)-7-Chloro-2',4,6-trimethoxy-6'-methylspiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, 5-18-05-00150 (Beilstein Handbook Reference), MLS001304062, MLS002152905, MLS002154239, BIDD:GT0024, DivK1c_000154, DivK1c_006432, GRISEOFULVIN [USP-RS], GRISEOFULVIN [WHO-DD], GRISEOFULVIN [WHO-IP], Griseofulvin (JAN/USP/INN), SPBio_000225, BPBio1_000299, MEGxm0_000184, orb1308779, orb3012982, orb3025493, SCHEMBL29379397, ACon0_000953, ACon1_001843, BDBM31775, Fulvicin-U/F Powder and Tablets, Griseofulvin - Bio-X trade mark, HMS500H16, KBio1_000154, KBio1_001376, KBio2_001296, KBio2_003864, KBio2_006432, KBio3_001121, GRISEOFULVIN [GREEN BOOK], NINDS_000154, GLXC-04995, GRISEOFULVIN [ORANGE BOOK], HMS1923E09, HMS2091A03, HMS2095N13, HMS2235F13, HMS3259D05, HMS3712N13, Pharmakon1600-00200046, GRISEOFULVIN [EP MONOGRAPH], (2S)-trans-7-Chloro-2',4,6-trimethoxy-6'-methylspiro(benzofuran-2[3H],1'-[2]cyclohexene)-3,4'-dione, 7-CHLORO-2',4,6-TRIMETHOXY-6'.BETA.-METHYLSPIRO(BENZOFURAN-2(3H),1'-(2)CYCLOHEXENE)-3,4'-DIONE, MSK21132, GRISEOFULVIN [USP MONOGRAPH], Tox21_111087, Tox21_202235, Tox21_303005, CCG-38416, EBC-14149, HY-17583R, LMPK13060001, NSC755822, s4071, GRISEOFULVINUM [WHO-IP LATIN], AKOS015896380, Tox21_111087_1, CS-3426, DB00400, FG23704, NC00616, SDCCGMLS-0066450.P001, IDI1_000154, NCGC00091120-02, NCGC00091120-03, NCGC00091120-04, NCGC00091120-05, NCGC00091120-06, NCGC00091120-07, NCGC00091120-08, NCGC00091120-09, NCGC00091120-13, NCGC00256353-01, NCGC00259784-01, (2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione, AS-13736, BT164513, HY-17583, SY071186, Griseofulvin 100 microg/mL in Acetonitrile, CS-0695022, G0384, NS00011725, EN300-52615, BIM-0051396.0001, C06686, D00209, AB00052005_07, Griseofulvin, VETRANAL(TM), analytical standard, F354301, GRISEOFULVIN PERMEABILITY DIAMETER [USP-RS], Q416096, SR-01000837512, doi:10.14272/DDUHZTYCFQRHIY-RBHXEPJQSA-N.1, SR-01000837512-2, SR-05000001535-1, SR-05000001535-3, SR-05000001535-4, BRD-K08273968-001-05-9, BRD-K08273968-001-09-1, BRD-K08273968-001-16-6, BRD-K08273968-001-19-0, Z756424454, Griseofulvin, British Pharmacopoeia (BP) Reference Standard, Griseofulvin, from Penicillium griseofulvum, 97.0-102.0%, Griseofulvin, European Pharmacopoeia (EP) Reference Standard, Griseofulvin, United States Pharmacopeia (USP) Reference Standard, Griseofulvin Permeability Diameter, United States Pharmacopeia (USP) Reference Standard, Griseofulvin, Pharmaceutical Secondary Standard, Certified Reference Material, (1'S,6'R)-7-Chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[[1]benzofuran-2,1'-cyclohex[2]ene]-3,4'-dione, 107912-37-8, 7-Chloro-2',4,6-trimethoxy-6'-methylspiro[benzofuran-2(3H),1',- [2]cyclohexene]-3,4'-dione, Spiro[benzofuran-2(3H),1-cyclohex[2]ene]-3,4-dione, 7-chloro-2,4,6-trimethoxy-6-methyl-, (2S,6R)-

Bioactivity: Antifungal antibiotic; inhibitor of fungal microtubule function and mitotic spindle assembly

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1,2-Dichloroethane	290.05	-	89.98	[123]
1,2-Dichloroethane	294.3	-	95.11	[123]
1,2-Dichloroethane	300.25	-	100.4	[123]
1,2-Dichloroethane	305.55	-	106.5	[123]
1,2-Dichloroethane	310.05	-	112.9	[123]
1,2-Dichloroethane	315.65	-	119.8	[123]
1,2-Dichloroethane	319.35	-	128.7	[123]
1,2-Dichloroethane	324.05	-	137.9	[123]
1,2-Dichloroethane	329.65	-	148.3	[123]
Acetone	281.95	-	31.83	[123]
Acetone	286.4	-	34.7	[123]
Acetone	291.85	-	37.62	[123]
Acetone	296.4	-	41.12	[123]
Acetone	300.8	-	45.11	[123]
Acetone	305.05	-	48.67	[123]
Acetone	310.25	-	55.43	[123]
Acetone	313.65	-	60.69	[123]
Acetone	317.05	-	67.24	[123]
Acetonitrile	278.15	-	22.82	[122]
Acetonitrile	283.15	-	25.27	[122]
Acetonitrile	288.15	-	28.43	[122]
Acetonitrile	293.15	-	31.97	[122]
Acetonitrile	298.15	-	35.97	[122]
Acetonitrile	303.15	-	40.78	[122]
Acetonitrile	308.15	-	46.21	[122]
Acetonitrile	313.15	-	52.4	[122]
Acetonitrile	318.15	-	58.86	[122]
Acetonitrile	323.15	-	66.44	[122]
Dimethyl sulfoxide	296.75	-	84.27	[123]
Dimethyl sulfoxide	301.15	-	93.24	[123]
Dimethyl sulfoxide	306.15	-	102.0	[123]
Dimethyl sulfoxide	310.85	-	108.8	[123]
Dimethyl sulfoxide	315.55	-	119.2	[123]
Dimethyl sulfoxide	320.55	-	129.3	[123]
Dimethyl sulfoxide	326.55	-	139.8	[123]
Dimethyl sulfoxide	331.95	-	149.2	[123]
Dimethyl sulfoxide	336.75	-	159.7	[123]
Dimethyl sulfoxide	341.05	-	169.8	[123]
Dimethyl sulfoxide	346.25	-	180.8	[123]
Dimethyl sulfoxide	351.7	-	192.5	[123]
Dimethyl sulfoxide	357.6	-	202.5	[123]
Dimethylacetamide	296.2	-	98.25	[123]
Dimethylacetamide	301.25	-	107.1	[123]
Dimethylacetamide	305.75	-	117.7	[123]
Dimethylacetamide	310.75	-	126.2	[123]
Dimethylacetamide	314.95	-	132.7	[123]
Dimethylacetamide	319.25	-	142.4	[123]
Dimethylacetamide	324.75	-	151.8	[123]
Dimethylacetamide	330.05	-	161.9	[123]
Dimethylacetamide	336.15	-	172.8	[123]
Dimethylacetamide	340.25	-	186.3	[123]
Dimethylacetamide	345.75	-	197.2	[123]
Dimethylacetamide	350.55	-	208.6	[123]
Dimethylacetamide	354.78	-	221.3	[123]
Dimethylformamide	278.15	-	22.62	[122]
Dimethylformamide	283.15	-	25.15	[122]
Dimethylformamide	288.15	-	28.26	[122]
Dimethylformamide	293.15	-	32.44	[122]
Dimethylformamide	298.15	-	37.28	[122]
Dimethylformamide	303.15	-	42.7	[122]
Dimethylformamide	308.15	-	48.45	[122]
Dimethylformamide	313.15	-	54.67	[122]
Dimethylformamide	318.15	-	61.35	[122]
Dimethylformamide	323.15	-	70.12	[122]
Ethanol	278.15	-	1.341	[122]
Ethanol	283.15	-	1.557	[122]
Ethanol	288.15	-	1.843	[122]
Ethanol	293.15	-	2.24	[122]
Ethanol	298.15	-	2.681	[122]
Ethanol	303.15	-	3.241	[122]
Ethanol	308.15	-	3.865	[122]
Ethanol	313.15	-	4.608	[122]
Ethanol	318.15	-	5.463	[122]
Ethanol	323.15	-	6.559	[122]
Methanol	278.15	-	2.185	[122]
Methanol	283.15	-	2.465	[122]
Methanol	288.15	-	2.908	[122]
Methanol	293.15	-	3.597	[122]
Methanol	298.15	-	4.48	[122]
Methanol	303.15	-	5.442	[122]
Methanol	308.15	-	6.593	[122]
Methanol	313.15	-	7.903	[122]
Methanol	318.15	-	9.398	[122]
Methanol	323.15	-	11.2	[122]
Methyl ethyl ketone	289.65	-	32.95	[123]
Methyl ethyl ketone	296.95	-	37.23	[123]
Methyl ethyl ketone	302.95	-	40.66	[123]
Methyl ethyl ketone	308.25	-	45.59	[123]
Methyl ethyl ketone	315.05	-	49.65	[123]
Methyl ethyl ketone	320.4	-	54.4	[123]
Methyl ethyl ketone	325.45	-	57.76	[123]
Methyl ethyl ketone	330.35	-	62.05	[123]
N-Methyl-2-pyrrolidone	278.15	-	124.5	[122]
N-Methyl-2-pyrrolidone	283.15	-	132.0	[122]
N-Methyl-2-pyrrolidone	288.15	-	141.6	[122]
N-Methyl-2-pyrrolidone	293.15	-	151.0	[122]
N-Methyl-2-pyrrolidone	295.55	-	161.1	[123]
N-Methyl-2-pyrrolidone	298.15	-	162.3	[122]
N-Methyl-2-pyrrolidone	300.65	-	172.5	[123]
N-Methyl-2-pyrrolidone	303.15	-	171.8	[122]
N-Methyl-2-pyrrolidone	305.75	-	183.2	[123]
N-Methyl-2-pyrrolidone	308.15	-	182.5	[122]
N-Methyl-2-pyrrolidone	310.0	-	195.2	[123]
N-Methyl-2-pyrrolidone	313.15	-	194.7	[122]
N-Methyl-2-pyrrolidone	315.1	-	206.1	[123]
N-Methyl-2-pyrrolidone	318.15	-	205.9	[122]
N-Methyl-2-pyrrolidone	320.6	-	216.7	[123]
N-Methyl-2-pyrrolidone	323.15	-	217.8	[122]
N-Methyl-2-pyrrolidone	325.45	-	228.5	[123]
N-Methyl-2-pyrrolidone	330.45	-	239.7	[123]
N-Methyl-2-pyrrolidone	335.55	-	252.7	[123]
N-Methyl-2-pyrrolidone	340.35	-	267.0	[123]
N-Methyl-2-pyrrolidone	345.55	-	287.9	[123]
N-Methyl-2-pyrrolidone	350.35	-	302.0	[123]
N-Methyl-2-pyrrolidone	355.65	-	314.8	[123]
Water	278.15	-	0.0038	[122]
Water	283.15	-	0.00489	[122]
Water	288.15	-	0.006	[122]
Water	293.15	-	0.0076	[122]
Water	298.15	-	0.0092	[122]
Water	303.15	-	0.0111	[122]
Water	308.15	-	0.014	[122]
Water	313.15	-	0.0173	[122]
Water	318.15	-	0.0214	[122]
Water	323.15	-	0.0263	[122]

Molecule 3D descriptors

Descriptor	Value
PMI1	1381.1885
PMI2	3247.4682
PMI3	3836.7913
NPR1	0.3600
NPR2	0.8464
RadiusOfGyration	3.4639
InertialShapeFactor	0.0006
Eccentricity	0.9330
Asphericity	0.2752
SpherocityIndex	0.3780
PBF	1.1820