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Antifungal

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Indrajeet Singh
Indrajeet Singh

This document discusses two types of antifungal drugs - those for local infections affecting areas like skin and those for systemic infections. It provides examples of chemical antifungal drugs like Tolnaftate and Undecylenic acid and antibiotic antifungals like Amphotericin, Nystatin, and Hamycin. For each drug, it describes properties, uses, brand names, and storage/stability considerations.

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T h e r e a r e t w o t y p e s o f a n t i f u n g a l d r u g s u s e d t o t r e a t i n f e c t i o n c a u s e d b y f u n g i . THEY ARE: -- D r u g s u s e d f o r t r e a t i n g l o c a l i n f e c t i o n s u c h a s t h o s e i n f e c t i n g h a i r , m u c o u s , m e m b r a n e s , n a i l s o r s k i n . T h e y a r e u s e d i n t h e f o r m o f o i n t m e n t s , c r e a m s , l i n i m e n t s , l o t i o n s , s u s p e n s i o n , s o l u t i o n s e t c . D r u g s u s e d f o r t r e a t i n g s y s t e m i c i n f e c t i o n s . I n p e r s o n s a f f l i c t e d w i t h a i d s s i n c e h o s t d e f e n c e m e c h a n i s m s b r e a k d o w n , f u n g i e a s i l y i n v a d e a n d c a u s e i n f e c t i o n s . a n t i f u n g a l a g e n t s m a y b e c l a s s i f i e d a s - - - - A n t i b i o t i c s a n d c h e m i c a l a n t i f u n g a l a g e n t s .
CLASSIFICATION:-- Chemical antifungal drugs :-- 1. Tolnaftate 2. Undecylenic acid Antibiotics:- 3. Amphotericin 4.Nystatin 5.Hamycin
TOLNAFTATE TOLNAFTATE IS A NAPTHALENE DERIVATIVE AND A THIOCARBAMATE. PROPERTIES It occurs as a white to creamy white powder. It is a odourless. It is practically insoluble in water. Freely soluble in acetone and chloroform and sparingly soluble in ether. It melts at 110 112*c . It is applied externally in fungal infection . STABILITY AND STORAGE:- It is stored in well closed containers. USES:- Antifungal drugs BRAND NAMES TINADERM , TOLNADERM, TONOFAL etc.
This is and unsaturated long chain fatty acid with one double Bond and 11 carbon atoms. CH2= CH-(CH2)8 COOH It is prepared by distilling castor oil in vacuum . the ricinoleic acid in castor oil is converted to undecylinic or undecenoic acid . PROPERTIES:-- It is a white yellow crystalline mass or a pale yellow liquid . It has a characteristics odour. It is practically insoluble in water and freely soluble in chloroform, ethanol, ether and in fixed oil.
Since it is unsaturated , it decolourises acidified potassium permanganate solution. STORAGE:-- Since undecenoic acid is unsaturated , it will be affected by Oxygen, of the atmosphere and also by light . This is catalysed by presence of some metals . So it must be stored in a well- closed , non-metallic containers , protected from light and at a temperature between 8 and 15*C. USES ANTIFUNGAL DRUGS. BRAND NAMES TINEAFAX, DECLIN, RENSELIN, SEVINON etc.
Amphotericin is an antifungal antibiotic obtained from Streptomyces Nodosus. It is a mixture of two substances, amphotericins A and B . The B compound is more active. Amphotericin B is a polyene antibiotic because it contains several double bonds. Its structure contains a macrocyclic ring. One side of the ring has seven conjugated double bonds. The other side contains several hydroxyl groups. At one end of the macrocyclic ring is attached a polar aminosugar (mycosamine) and also a corboxylic acid group. As its name implies , amphotericin is amphoteric in nature.
PHYSICAL PROPERTIES:-- Amphotericin B is a yellow to orange powder without any odour. It decomposes gradually around 170*C. The solids and its solution are stable between pH 4 to 10 when stored at a cold temperature without being exposed to air and light . It gradually decomposes when humidity is high . It also decomposes faster when temperature is high. It is soluble in dimethyl sulphoxide and slightly soluble in methanol and dimethyl formamide. CHEMICAL PROPERTIES:-- When phosphoric acid is added to a solution of the substance in dimethyl sulphoxide a blue ring is immediately formed at the junction of the test tube.
When it is mixed , the mixture becomes intensely blue . If water is added and mixed , the solution gets a pale straw yellow colour. Storage :-- Store in tightly- closed resistant containers in a cold and dry place. Uses:-- Antifungal drugs Brand names Mysteclin (amphotericin b with tetracycline) Fungizone otic (ear drops) Fungi zone intravenous
NYSTATIN IS AN ANTIFUNGALANTIBIOTIC OBTAINED FROM STREPTOMYCES NOURSEI . It is also a polyene antibiotic containing a macrocyclic ring. It has a conjugated tetraene system and also a diene. The polar aminosugar attached to the ring is mycosamine as in amphotericin
PHYSICAL PROPERTIES:-- It is a yellow to slightly brown powder with a characteristic odour. It is hygroscopic. It has strong reducing properties. It is slightly soluble in water and freely soluble in dimethyl fromamide. It is slightly soluble in methanol and insoluble in chloroform, ether and ethanol (95%). It is affected by light, heat and , moisture and when exposed to air. Its solution are inactivated by acids and bases.
CHEMICAL PROPERTIES :- i. It gives brown colour with HCL. ii. And with sulphuric acid also a brown colour is produced but it becomes violet on standing. iii. It gives a green colour when its aqueous solution is shaken with a solution of sodium molybdo phosphotungstate. , when aqueous solution is shaken with decolourised magenta solution containing a little pyrogallol dissolved in it ,a dark pink colour is produced , even after standing for one hour , the colour is retained. USES:-- i. ANTIFUNGALANTIBIOTIC BRAND NAMES -- Mycostatin Nystatin eye (eye ointment) Fungicidin Candex etc.
STORAGE:-- IT SHOULD BE STORED IN WELL TIGHT CLOSED CONTAINERS. USES:-- ANTIFUNGALANTIBIOTIC BRAND NAMES --- MYCOSTATIN NYSTIN (Eye Ointment) FUNGICIDIN CANDEX, etc.
HAMYCIN IS AN ANTIFUNGALANTIBIOTIC ISOLATED FROM THE FILTRATE OS STREPTOMYCES PIMPRINA IT IS A POLYENE COMPOUND LIKE AMPHOTERICIN AND NYSTATIN . HAMYCIN IS A MIXTURE OF COMPONENTS A, B , C AND D. PROPERTIES :-- It is a yellow amorphous compound . It is very slightly soluble in water , ethanol, benzene, & chloroform etc. It is soluble in aqueous alcohols and basic solvents like pyridine. It is amphoteric.
USES ANTIFUNGALANTIBIOTIC BRAND NAMES HAMYCIN IMPRIMA PRIMAMYCIN

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  • 1. T h e r e a r e t w o t y p e s o f a n t i f u n g a l d r u g s u s e d t o t r e a t i n f e c t i o n c a u s e d b y f u n g i . THEY ARE: -- D r u g s u s e d f o r t r e a t i n g l o c a l i n f e c t i o n s u c h a s t h o s e i n f e c t i n g h a i r , m u c o u s , m e m b r a n e s , n a i l s o r s k i n . T h e y a r e u s e d i n t h e f o r m o f o i n t m e n t s , c r e a m s , l i n i m e n t s , l o t i o n s , s u s p e n s i o n , s o l u t i o n s e t c . D r u g s u s e d f o r t r e a t i n g s y s t e m i c i n f e c t i o n s . I n p e r s o n s a f f l i c t e d w i t h a i d s s i n c e h o s t d e f e n c e m e c h a n i s m s b r e a k d o w n , f u n g i e a s i l y i n v a d e a n d c a u s e i n f e c t i o n s . a n t i f u n g a l a g e n t s m a y b e c l a s s i f i e d a s - - - - A n t i b i o t i c s a n d c h e m i c a l a n t i f u n g a l a g e n t s .
  • 2. CLASSIFICATION:-- Chemical antifungal drugs :-- 1. Tolnaftate 2. Undecylenic acid Antibiotics:- 3. Amphotericin 4.Nystatin 5.Hamycin
  • 3. TOLNAFTATE TOLNAFTATE IS A NAPTHALENE DERIVATIVE AND A THIOCARBAMATE. PROPERTIES It occurs as a white to creamy white powder. It is a odourless. It is practically insoluble in water. Freely soluble in acetone and chloroform and sparingly soluble in ether. It melts at 110 112*c . It is applied externally in fungal infection . STABILITY AND STORAGE:- It is stored in well closed containers. USES:- Antifungal drugs BRAND NAMES TINADERM , TOLNADERM, TONOFAL etc.
  • 4. This is and unsaturated long chain fatty acid with one double Bond and 11 carbon atoms. CH2= CH-(CH2)8 COOH It is prepared by distilling castor oil in vacuum . the ricinoleic acid in castor oil is converted to undecylinic or undecenoic acid . PROPERTIES:-- It is a white yellow crystalline mass or a pale yellow liquid . It has a characteristics odour. It is practically insoluble in water and freely soluble in chloroform, ethanol, ether and in fixed oil.
  • 5. Since it is unsaturated , it decolourises acidified potassium permanganate solution. STORAGE:-- Since undecenoic acid is unsaturated , it will be affected by Oxygen, of the atmosphere and also by light . This is catalysed by presence of some metals . So it must be stored in a well- closed , non-metallic containers , protected from light and at a temperature between 8 and 15*C. USES ANTIFUNGAL DRUGS. BRAND NAMES TINEAFAX, DECLIN, RENSELIN, SEVINON etc.
  • 6. Amphotericin is an antifungal antibiotic obtained from Streptomyces Nodosus. It is a mixture of two substances, amphotericins A and B . The B compound is more active. Amphotericin B is a polyene antibiotic because it contains several double bonds. Its structure contains a macrocyclic ring. One side of the ring has seven conjugated double bonds. The other side contains several hydroxyl groups. At one end of the macrocyclic ring is attached a polar aminosugar (mycosamine) and also a corboxylic acid group. As its name implies , amphotericin is amphoteric in nature.
  • 7. PHYSICAL PROPERTIES:-- Amphotericin B is a yellow to orange powder without any odour. It decomposes gradually around 170*C. The solids and its solution are stable between pH 4 to 10 when stored at a cold temperature without being exposed to air and light . It gradually decomposes when humidity is high . It also decomposes faster when temperature is high. It is soluble in dimethyl sulphoxide and slightly soluble in methanol and dimethyl formamide. CHEMICAL PROPERTIES:-- When phosphoric acid is added to a solution of the substance in dimethyl sulphoxide a blue ring is immediately formed at the junction of the test tube.
  • 8. When it is mixed , the mixture becomes intensely blue . If water is added and mixed , the solution gets a pale straw yellow colour. Storage :-- Store in tightly- closed resistant containers in a cold and dry place. Uses:-- Antifungal drugs Brand names Mysteclin (amphotericin b with tetracycline) Fungizone otic (ear drops) Fungi zone intravenous
  • 9. NYSTATIN IS AN ANTIFUNGALANTIBIOTIC OBTAINED FROM STREPTOMYCES NOURSEI . It is also a polyene antibiotic containing a macrocyclic ring. It has a conjugated tetraene system and also a diene. The polar aminosugar attached to the ring is mycosamine as in amphotericin
  • 10. PHYSICAL PROPERTIES:-- It is a yellow to slightly brown powder with a characteristic odour. It is hygroscopic. It has strong reducing properties. It is slightly soluble in water and freely soluble in dimethyl fromamide. It is slightly soluble in methanol and insoluble in chloroform, ether and ethanol (95%). It is affected by light, heat and , moisture and when exposed to air. Its solution are inactivated by acids and bases.
  • 11. CHEMICAL PROPERTIES :- i. It gives brown colour with HCL. ii. And with sulphuric acid also a brown colour is produced but it becomes violet on standing. iii. It gives a green colour when its aqueous solution is shaken with a solution of sodium molybdo phosphotungstate. , when aqueous solution is shaken with decolourised magenta solution containing a little pyrogallol dissolved in it ,a dark pink colour is produced , even after standing for one hour , the colour is retained. USES:-- i. ANTIFUNGALANTIBIOTIC BRAND NAMES -- Mycostatin Nystatin eye (eye ointment) Fungicidin Candex etc.
  • 12. STORAGE:-- IT SHOULD BE STORED IN WELL TIGHT CLOSED CONTAINERS. USES:-- ANTIFUNGALANTIBIOTIC BRAND NAMES --- MYCOSTATIN NYSTIN (Eye Ointment) FUNGICIDIN CANDEX, etc.
  • 13. HAMYCIN IS AN ANTIFUNGALANTIBIOTIC ISOLATED FROM THE FILTRATE OS STREPTOMYCES PIMPRINA IT IS A POLYENE COMPOUND LIKE AMPHOTERICIN AND NYSTATIN . HAMYCIN IS A MIXTURE OF COMPONENTS A, B , C AND D. PROPERTIES :-- It is a yellow amorphous compound . It is very slightly soluble in water , ethanol, benzene, & chloroform etc. It is soluble in aqueous alcohols and basic solvents like pyridine. It is amphoteric.
  • 14. USES ANTIFUNGALANTIBIOTIC BRAND NAMES HAMYCIN IMPRIMA PRIMAMYCIN