MEDICINAL CHEMISTRY

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O O OH 4- Hydroxycoumarin (29) + O 2N CH=CHCOCH 3 O OH O C H Nicoumalone (34) Stryl ketone (37) CH 2COCH 3 Tromexan or Pelentan (Ethyl biscoumacetate) (40): Chemically ethyl-bis (4hydroxycoumarin-3-yl)-acetate, is an analogue of dicoumarol. It is used as oral anticoagulant, and for quicker in action. It can be prepared by condensing 4hydroxycoumarin (29) and glyoxalic acid (38) in the following way: O OH O 4- Hydroxycoumarin (29) + O O OH COOH CHO O O CH + Glyoxalic acid (38) Dil AcOH O O CH OH COOH (39) O OH O OH O EtOH/ Conc H 2SO 4 or HCl COOEt Tromexan (40) O NO 2 OH 4- Hydroxycoumarin (29)
Warfarin and other coumarin derivatives are antagonists of vitamin K. Thus they act by depressing the vitamin K-dependent synthesis of coagulation factors 11 (prothrombin), VII, IX and X, and of the anticoagulant protein C and its protein cofactor protein S. Official Drugs Warfarin Sodium, B.P., I.P.: Warfarin sodium is the sodium salt of (RS)-4-hydroxy-3- (3-oxo-l-phenylbutyl)-coumarin. It is a white powder and hygroscopic. It is very soluble in water. It should be kept in an airtight container and protected from light. Warfarin sodium is readily absorbed from the gastrointestinal tract. It can also be absorbed through the skin. It is extensively bound to plasma proteins and its plasma half-life is about 37 hours. Warfarin is transformed into inactive metabolites by the liver and kidneys. They are excreted in urine and stool. Warfarin is used in the prevention and treatment of deepvein thrombosis or pulmonary embolism. It is equally effective either orally or intravenously. Warfarin should not be given to patients who are haemorrhaging, Warfarin is used as a racemic mixture, and however the S-isomer is reported to be more potent. Usual dose of warfarin sodium is 10 mg daily by mouth for 2 days, but may be lower for patients with particular risk of haemorrhage. Subsequent maintenance doses usually range from 3 to 9 mg daily. Preparation: Warfarin Tablets, B.P. Proprietary Names: COUMADIN; PANWARFIN Warfarin Sodium tablets, I.P Warfarin Sodium Clathrate, B.P., I.P.: Warfarin sodium Clathrate is the Clathrate of the sodium salt of (RS)-4-hydroxy-3-(3-oxo-l-phenylbutyl)-coumarin with propan-2-ol. It consists of warfarin sodium and propan-2-ol in the molecular proportion of 2:1. It contains approximately 92% of warfarin sodium. It is a white powder and is very soluble in water. It should be kept in an airtight container and protected from light. It has actions and uses similar to those of warfarin sodium. Preparation: Warfarin Tablets, B.P. Acenocoumarin/Nicoumalone, B.P, I.P.: Nicoumalone is (RS)-4-hydroxy-3-[1-(4nitrophenyl)-3-oxobutyl] coumarin. It is a white to brownish white powder, practically insoluble in water. It is stored in light-resistant containers. Nicoumalone is readily absorbed when given by mouth. It is excreted chiefly in the urine mainly as metabolites. It is extensively bound to plasma proteins. Nicoumalone has actions and uses similar to those of warfarin sodium. It is administered orally. Though used as a racemic mixture, the R(+)-enantiomer of nicoumalone is reported to be pharmacologically active component of nicoumalone. The initial dose of nicoumalone is 12 to 20 mg; subsequent doses are given in accordance with the needs of the patient. Preparation: Nicoumalone Tablets, B.P., I.P. Proprietary Name: SINTHROME C. Indanedione Indanedione derivatives, such as phenindione and anisidione, were conceived as ring contracted analogues of coumarins. Like coumarins they also act as oral anticoagulants by inhibiting the synthesis of prothrombin and other factors VII, IX and X.
Page 1 and 2: CONTENTS Antianginal Drugs Anticoag
Page 3 and 4: c) Dihydropyridine derivative: e.g.
Page 5 and 6: 2 (d) 4. H 3C H 3C HO CH-CH 2-O-CH
Page 7 and 8: pentaerythritol, and is supplied di
Page 9 and 10: of' streptokinase, urokinase and ti
Page 11 and 12: Low-molecular-weight Heparins, B.P.
Page 13: OH COOCH 3 AC 2O Methyl salicylate
Page 17 and 18: Structure-activity Relationship All
Page 19 and 20: Mean Arterial Blood Pressure (MABP)
Page 21 and 22: Table-1 ---------------------------
Page 23 and 24: Ramipril Altace ( Hoechst-Marion) 2
Page 25 and 26: Official drugs: Prazosin Hydrochlor
Page 27 and 28: treatment of hypertension, the dosa
Page 29 and 30: NH ClCH 2CN NCH 2CN Perhydroazocine
Page 31 and 32: B (2). Angiotensin Receptor Antagon
Page 33 and 34: CH3COOC2H5 Diazoxide (90) Cl NH 2 S
Page 35 and 36: Structure-activity Relationships of
Page 37 and 38: N N R Acidic group (102) Acidic gro
Page 39 and 40: Structure-activity Relationships of
Page 41 and 42: HO HO HO HO H 3C CH 3 H Digitoxigen
Page 43 and 44: efractory periods. These are mainly
Page 45 and 46: Structure - Activity Relationship:
Page 47 and 48: Hydralazine is a direct relaxant of
Page 49 and 50: K4[Fe(CN) 6].3H2O + 6HNO3 H2[(NO)Fe
Page 51 and 52: conduction velocity, and decrease s
Page 53 and 54: Synthesis of Moricizine: (153) H N
Page 55 and 56: Tocainide Hydrochloride (±)-2-Amin
Page 57 and 58: influx through β-receptor blockade
Page 59 and 60: Cl Cl CH2CH=CH2 N N N H Alinidine (
Page 61 and 62: (iii) Intermediate density lipoprot
Page 63 and 64: Structure-activity Relationship Mev
Page 65 and 66:
to the bile acids. Thus due to ente
Page 67 and 68:
moderate reduction in cholesterol l
Page 69 and 70:
(iii) Other types: (a) Insulin rece
Page 71 and 72:
non-crystalline insulin as far as o
Page 73 and 74:
for better drug in this series. Sub
Page 75 and 76:
Key to general structure X SO 2 NH
Page 77 and 78:
Official Drugs: Insulin, B.P. It is
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MEDICINAL CHEMISTRY

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