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(+)-Griseofulvin

General description Physical and Chemical Properties Pharmacological effects Pharmacokinetics Indications Side effects Precautions Drug Interactions Toxicity Pediatric medication Elderly medication Chemical Properties Production methods Category Toxicity grading Acute toxicity Flammability hazard characteristics Storage Characteristics Extinguishing agent
(+)-Griseofulvin
(+)-Griseofulvin
CAS No.
126-07-8
Chemical Name:
(+)-Griseofulvin
Synonyms
Fulcin;Gricin;Griseo;Grysio;Poncyl;Amudane;Fulcine;Fulvina;Greosin;Lamoryl
CBNumber:
CB1766075
Molecular Formula:
C17H17ClO6
Formula Weight:
352.77
MOL File:
126-07-8.mol

(+)-Griseofulvin Properties

Melting point:
218-220 °C(lit.)
alpha 
354 º (c=1, dimethylform)
Boiling point:
469.04°C (rough estimate)
Density 
1.2579 (rough estimate)
refractive index 
1.4429 (estimate)
storage temp. 
−20°C
form 
Powder
color 
White to yellow-white
Water Solubility 
practically insoluble
λmax
321nm(CHCl3)(lit.)
Merck 
14,4549
BRN 
95226
InChIKey
DDUHZTYCFQRHIY-RBHXEPJQSA-N
CAS DataBase Reference
126-07-8(CAS DataBase Reference)
NIST Chemistry Reference
Griseofulvin(126-07-8)
EPA Substance Registry System
Spiro[benzofuran- 2(3H),1'-[2]cyclohexene]- 3,4'-dione, 7-chloro-2',4,6-trimethoxy- 6'-methyl-, (1'S,6'R)-(126-07-8)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  T,Xn
Risk Statements  60-61-40-43-45
Safety Statements  53-22-36/37/39-45
WGK Germany  3
RTECS  WG9800000
Hazardous Substances Data 126-07-8(Hazardous Substances Data)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H317 May cause an allergic skin reaction Sensitisation, Skin Category 1 Warning P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H340 May cause genetic defects Germ cell mutagenicity Category 1A, 1B Danger
H351 Suspected of causing cancer Carcinogenicity Category 2 Warning P201, P202, P281, P308+P313, P405,P501
H360 May damage fertility or the unborn child Reproductive toxicity Category 1A, 1B Danger
H371 May cause damage to organs Specific target organ toxicity, single exposure Category 2 Warning P260, P264, P270, P309+P311, P405,P501
H373 May cause damage to organs through prolonged or repeated exposure Specific target organ toxicity, repeated exposure Category 2 Warning P260, P314, P501
Precautionary statements:
P201 Obtain special instructions before use.
P202 Do not handle until all safety precautions have been read and understood.
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P308+P313 IF exposed or concerned: Get medical advice/attention.
P405 Store locked up.
P501 Dispose of contents/container to..…

(+)-Griseofulvin price More Price(16)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1299007 Griseofulvin United States Pharmacopeia (USP) Reference Standard 126-07-8 200mg $348.4 2017-11-08 Buy
Sigma-Aldrich 1299200 Griseofulvin Permeability Diameter United States Pharmacopeia (USP) Reference Standard 126-07-8 2g $348.4 2017-11-08 Buy
TCI Chemical G0384 (+)-Griseofulvin >97.0%(HPLC) 126-07-8 5g $27 2017-11-08 Buy
TCI Chemical G0384 (+)-Griseofulvin >97.0%(HPLC) 126-07-8 25g $78 2017-11-08 Buy
Alfa Aesar B23521 (+)-Griseofulvin, 97% 126-07-8 25g $108 2017-11-08 Buy

(+)-Griseofulvin Chemical Properties,Uses,Production

General description

Griseofulvin is a non-polyene class antifungal antibiotics; it can strongly inhibit the mitosis of fungal cell and interfere with the fungal DNA synthesis; it can also bind to tubulin to prevent fungal cell division. It has been applied to clinical medicine since 1958 and has currently been widely used for treating the fungal infections of the skin and the stratum corneum with strong inhibitory effects on Trichophyton rubrum and Trichophyton tonsorans, etc. Griseofulvin is not only a widely used antibiotic for clinical treatment of fungal infections of the skin and cuticle, but also applied in agriculture for prevention and treatment of fungal diseases; for example, it has a special efficacy on treating a kind of candidiasis in apple which can cause infection during pollination.

Physical and Chemical Properties

Griseofulvin pure product is colorless crystal, being neutral, and insoluble in water with a strong systemic property. It is stable both in vitro and in vivo of plants and is also stable to the various environment factors between pH3.0~8.8. It can be used for prevention and treatment of a variety of fungal plant diseases. The main species china applied for production of griseofulvin is Penicillium nigricans and Penicillium urticae. When grown at the medium, Penicillium nigricans is fuzzy with fresh culture being pure gray and aging culture being dark gray with its back being deep orange-red to the back orange brown. The fungi lawn of Penicillium urticae is yellowish green to pure light gray, thick and dense with the back being pale yellow to brownish; their aerial hyphae has a broom-like shape.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Pharmacological effects

In medicine, this product mainly has good antibacterial effect against Trichophyton, Microspores, and Epidermophyton fungi. However, it has no anti-bacterial effect on Candida, Cryptococcus, Histoplasma, Sporothrix, Blastomyces, and Coccidioides and so on. Mechanism of action of is drug is through interfering with the biosynthesis of nucleic acids of fungal and further inhibiting of its growth.
In agriculture, this product has good inhibitory effect on the Ascomycetes, Basidiomycetes, Deuteromycetes and some kinds of algae. However, it is not effective in treating oomycetes whose cell wall containing no chitin content. After spraying melons and other crops, it can be transferred into the branch, leaves and fruits through inner absorption, the absorption of water via rrot, as well as transpiration effect, and further preventing the fungal diseases; according to the study of Brandeis et al. (1946), at a concentration as low as even 10 mg/L or 1 mg/L, griseofulvin can already can make the mycelium of Bctrytis allill be stout, deformed and exhibit spiral bending, also cause: large number of abnormal branching; the development retardation of germinated spores, and loss of apical dominance; thus it has uptake therapeutic effects on a variety of plant diseases, especially powdery mildew, gray mold diseases; Griseofulvin has a more prominent antibacterial activity than the bactericidal activity.

Pharmacokinetics

The absorption of orally administration of this drug varies according to the difference in preparation, the micro-particle of this drug can be absorbed by 25% to 70%; its ultrafine particles can almost all absorbed after oral administration. Eating fat can significantly increase the extent of absorption. The product has a serum protein binding rate of being 80%. After its absorption, this product can be deposited in the skin, hair, nail cuticle and combine with keratin to prevent the further invasion of sensitive dermatophytes; at the same time, the pathogenic fungi locate in superficial stratum corneum will leave the body together with the fall-off of the skin or hair with only a very small amount being distribution in other body fluids and tissues. This product can also enter into the fetal circulation and be secreted from the milk. This product is inactivated through metabolism in the liver with the main metabolite being 6-methyl griseofulvin and glucuronic acylate; the blood elimination half-life is 14 to 24 hours. The percentage of product secreted from the urine in its prototype is less than 1% with about 16% to 36% of the prototype being discharged from the feces.

Indications

In medicine, this product is suitable for the treatment of a variety of ringworm, including tinea capitis, tinea barbae, body tinea, jock itch, foot tinea and onychomycosis. The various kinds of tinea mentioned are caused by various fungi including Trichophyton rubrum, Trichophyton tonsorans, Trichophyton mentagrophytes, Fingers Trichophyton, etc., and Microsporon audouini, Microsporon canis, Microsporon gypseum and Epidermophyton floccosum, etc. due. This product is not suitable for treatment in mild cases, localized infection cases and cases which can be treated with topical antifungal agents. Griseofulvin is not effective in treating the infections of a various kinds of fungi such as Candida, Histoplasma, Actinomyces, Sporothrix species, Blastomyces, Coccidioides, Nocardio and Cryptococcus species as well as treating tinea versicolor.
In agriculture, this product is first introduced by Brian et al (1951) for control of plant diseases. According to previous studies, it can be used for prevention of melon (melon) vine blight, crack spread disease, watermelon blight, anthracnose, apple blossom rot, apple cold rot, apple rot, cucumber downy mildew , strawberry gray mold, gourds hanging blight, powdery mildew of roses, chrysanthemums powdery mildew, rot flower lettuce, early tomato blight, tulip fire blight and other fungal diseases.

Side effects

1. Nervous system headache is relatively common with about 10% of patients experiencing headaches; it is a bit severe at initial stage, but will be alleviated with the continuing administration of drug; other reactions also include lethargy and fatigue. Occasional dizziness, ataxia, and peripheral neuritis may also occur.
2. For Digestive system; a small number of patients may undergo abdominal discomfort, nausea or diarrhea, usually mild which can be tolerated by the patient.
3. Allergies can occur in about 3% of patients which suffers rash; occasionally angioneurotic edema, persistent urticaria, and exfoliative dermatitis can also occur; in very rare cases, photosensitive dermatitis can occur at a small number of patients.
4. This product can sometimes cause reduction of the number of peripheral blood leukocyte; sometime can even cause liver toxicity and proteinuria.

Precautions

1. Cross allergy; because griseofulvin is obtained from Penicillium, which indicated that the drug may have cross-allergy with penicillin or penicillamine, however, this kinds of hypothesis hasn’t been confirmed by clinical cases; but patients allergic to penicillin should still apply with caution and subject to careful observation.
2. Griseofulvin can cause tumor in animal experiments.
3. This product can occasionally cause liver toxicity; patients with original liver disease or liver damage should decide whether to choose to apply this drug after thinking twice.
4. It can induce porphyria and lupus; lupus patients who have index should have trade-off decision before applying this drug.
5. During the treatment, regular testing of peripheral blood, liver function, blood nitrogen content in urea, creatinine and urine routine are demanded.
6. It can be administrated either simultaneously with meal or after the meal with high-fat meal being the best, because they can reduce the gastrointestinal side effects and increase drug absorption.
7. In order to prevent relapse, treatment should be continued until clinical symptoms and laboratory tests confirmed that the pathogen has been completely eradicated. Usually treatment course is: tinea capitis: 8 to 10 weeks; tinea: 2 to 4 weeks; tinea pedis: 4-8 weeks; finger nail tinea: at least four months; nail psoriasis: at least six months, although still with a high recurrence rate.
8. A suitable topical administration is usually necessary at the same time; this is particularly important for athlete's foot.
9. During the treatment or at least 6 months of post-treatment, male patients should take contraceptive measures for prevention of pregnancy.

Drug Interactions

1. Combination of this product together with ethanol can cause tachycardia, sweating, flushing of the skin, etc., so avoid taking them at the same time.
2. Combination with anticoagulant drugs such as warfarin, and coumarin can enhance the hepatic metabolism and leaving the efficacy of anticoagulation being weakened; so it is necessary to adjust the dose by monitoring the prothrombin time at the same time.
3. Combination with primidone, and phenobarbital can decrease the antifungal effect of this product which may be due to that absorption of barbiturates may reduce the absorption of this drug as well as the increased rate of its inactivation due to the induction of hepatic enzyme which causes the decreased blood concentration; thus should avoid this kind of combination of drugs.
4. Combination of estrogen-class contraceptive with the product can reduce the effect of orally administrated contraceptives which may be due to that the product may strengthen the metabolism of contraceptive drugs in the live, causing its decreased blood concentration; thus should avoid using them simultaneously.

Toxicity

Griseofulvin has a relatively low toxicity to warm-blooded animals; intraperitoneal injection of both sexes of Waster rats found that they could both withstand a dosage of per 100ml/kg (some damage effects on the seminal vesicles and the intestinal epithelium were observed). Although intravenous injection can cause the temporary inhibition of cells mitosis (especially bone marrow some cells), the rates were almost unaffected under normal conditions. Moreover, after 24 hours, the rats began to rapidly recover; its LD50 is 400ml/kg body weight. Furthermore, even a large dose of griseofulvin only has a very small toxicity to the plants. It will be slowly degraded in the body with a faster degradation rate in soil; so there are no issues about residue and environmental pollution problems. However, the property of its fast degradation also limits their application of antimicrobial activity in agriculture.

Pediatric medication

We are lack of information about the medication on children under 2 years.

Elderly medication

There are still no existing information about its application in Elderly people and the relation with their ages.

Chemical Properties

It is white or white-like powder. Melting point is 218-224 °C. It is highly soluble in tetrachloroethane, soluble in acetone or chloroform, slightly soluble in methanol or ethanol, and very slightly soluble in water. It is odorless or almost odorless with slightly bitter taste. It is stable to heat.

Production methods

Griseofulvin is a antibiotic produced from the culture fermentation broth of Penicillium griseofulvum.

Chemical Properties

Crystalline Solid

Category

Pesticide

Uses

adrenegic blocker, Ca channel blocker, coronary vasodilator, antiarrhythmic

Uses

antifungal, inhibits mitosis in metaphase

Uses

Griseofulvin is a spirobenzofuran produced by a number of Penicillium species, first isolated in the 1930s by Raistrick's group. Griseofulvin is a selective antifungal agent used to treat skin infections in animals and humans. Griseofulvin acts by binding to fungal tubulin and inhibiting the mitotic spindle. Griseofulvin's ability to bind to keratin is considered an important aspect of the metabolite's access to dermatophytic fungi. More recently, griseofulvin has become an important phenotypic marker in Penicillium taxonomy.

Uses

An antifungal and antiproliferative agent that affects microtubules.

Uses

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

Definition

ChEBI: An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.

Toxicity grading

Low toxicity

Acute toxicity

Oral-rat LD50: 10000 mg/kg; Oral-Mouse LD50: 50000 mg/kg

Flammability hazard characteristics

Combustion can produce toxic chloride gas

Storage Characteristics

Treasury: ventilation low-temperature an dry; it should be separately stored and transported from raw materials of food.

Extinguishing agent

Dry powder, foam, sand

General Description

White to pale cream-colored crystalline powder. Odorless or almost odorless. Tasteless. Sublimes without decomposition at 410°F.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

(+)-Griseofulvin is incompatible with strong oxidizing agents. .

Fire Hazard

Flash point data for (+)-Griseofulvin are not available. (+)-Griseofulvin is probably combustible.

Purification Methods

Crystallise it from *benzene or EtOH. Purify 2g of griseofulvin by chromatography on Alumina (40 x 1.5cm) and elute with *C6H6/MeOH (199:1) and follow the UV blue fluorescent band. [MacMillan J Chem Soc 1823 1959, Beilstein 18 III/IV 3160, 18/5 V 150.]

(+)-Griseofulvin Preparation Products And Raw materials

Raw materials

Preparation Products


(+)-Griseofulvin Suppliers

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