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Basic Information

Molecular Structure:
CAS No.:	36791-04-5
Name:	Ribavirin
Article Data:	46

Formula:	C₈H₁₂N₄O₅
Molecular Weight:	244.207
Synonyms:	Tribavirin;Ribavirin (JAN/USP);Virazole;Ribamide;Virazid;1,2,4-Triazole-3-carboxamide, 1-.beta.-D-ribofuranosyl-;Vilona;1H-1,2,4-Triazole-3-carboxamide, 1-.beta.-D-ribofuranosyl-;ICN 1229;1-.beta.-D-Ribofuranosyl-1H-1,2, 4-triazole-3-carboxamide;Rebetol;Virazole (TN);Rebretron;1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide;ICN-1229;1-.beta.-D-Ribofuranosyl-1,2,4-triazolo-3-carboxamide;Ribamidil;Copegus;1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide; 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione;RTCA;RTC;RBV;1H-1,2,4-Triazole-3-carboxamide,1-a-Dribofuranosyl-;1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide;RCTA;Viramid;Ribavirin (Virazole);1-β-d-ribofuranosyl-1,2,4-triazole-3-carboxamide;Ribavirin EP5;
EINECS:	636-825-3
Density:	2.086 g/cm³
Melting Point:	174-176 °C
Boiling Point:	639.782 °C at 760 mmHg
Flash Point:	340.728 °C
Solubility:	>=10 g/100 mL at 19 °C in water
Appearance:	Colourless solid
Hazard Symbols:	T, Xi
Risk Codes:	61-36/38
Safety:	53-22-45-37/39-26
PSA:	143.72000
LogP:	-2.31120

Synthetic route

: 57198-04-6, 39925-10-5
1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester

: 36791-04-5
ribavirin

Conditions

Conditions	Yield
With ammonia at 20℃; under 5250.53 Torr; for 20h; Temperature; Pressure; Autoclave; Green chemistry;	99.71%
With ammonia In methanol at 0℃; for 2.5h; Temperature; Solvent;	97%
With methanol; ammonia at 10 - 20℃; for 18h; Autoclave;	92.6%

: 38934-69-9
methyl 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylate

: 36791-04-5
ribavirin

Conditions

Conditions	Yield
With sodium methylate; diethylamine In methanol at 80℃; for 6h; Solvent;	95%
With ammonia In methanol at 20℃; for 4h;
With ammonia In methanol for 5h; Autoclave;	107.52 g
With ammonia In methanol at 20℃; for 4h;

: 40371-99-1
3-cyano-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-triazole

: 36791-04-5
ribavirin

Conditions

Conditions	Yield
With ammonium hydroxide; dihydrogen peroxide; platinum In methanol	51.2%
Multi-step reaction with 3 steps 1: methanol / 2 h / 25 °C 2: methanol / 1 h / 50 °C 3: pH 7.4, phosphate buffer / Ambient temperature View Scheme

: 3641-08-5
1,2,4-triazole-3-carboxamide

: 58-96-8
uridine

: 36791-04-5
ribavirin

Conditions

Conditions	Yield
With Enterobacter gergoviae CECT 875 in agar In phosphate buffer at 60℃; for 3h; pH=7.0; Enzymatic reaction;	45%
With potassium phosphate buffer at 60℃; for 24h; Enterobakter aerogenes AJ 1125;
With Geobacillus kaustophilus ATCC 8005 entrapped in agarose matrix supplemented with bentonite In aq. phosphate buffer at 60℃; for 6h; pH=7; Reagent/catalyst; Green chemistry;

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 13035-61-5
1,2,3,5-tetraacetylribose

: 36791-04-5
ribavirin

Conditions

Conditions	Yield
With Bis(p-nitrophenyl) phosphate at 80 - 147℃; for 0.833333h; Temperature; Large scale;	77.1%

: 58151-90-9
ribavirin benzoate

: 36791-04-5
ribavirin

Conditions

Conditions	Yield
With pyrographite In dichloromethane; acetonitrile at 60℃; for 0.333333h;	90.16 g

: 1-trimethylsilyl-1H-1,2,4-triazole-3-carboxamide

: 13035-61-5
1,2,3,5-tetraacetylribose

: 36791-04-5
ribavirin

Conditions

Conditions	Yield
Stage #1: 1-trimethylsilyl-1H-1,2,4-triazole-3-carboxamide With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane at 95℃; for 5h; Stage #2: 1,2,3,5-tetraacetylribose With tin(ll) chloride In dichloromethane at 0℃; Temperature;

: 3641-08-5
1,2,4-triazole-3-carboxamide

: 118-00-3
G

: 36791-04-5
ribavirin

Conditions

Conditions	Yield
With 1A cells; E. coli BMT 4D In phosphate buffer at 60℃; for 30h; pH=7.5;	70%
With phosphate buffer; purine nucleoside phosphorylase immobilised on AP-CPG-170 In water at 60℃; for 36h; pH=7.0;	68%
at 60℃; catalyzation by purine nucleoside phosphorylase of Brevibacterium acetylicum ATCC 954, potassium phosphate buffered at pH 7.0; Yield given;

: 535960-09-9
(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(3-(ethoxycarbonyl)-1H-1,2,4-triazol-1-yl)tetrahydrofuran-3,4-diyl diacetate

: 36791-04-5
ribavirin

Conditions

Conditions	Yield
With ammonia In methanol at 20℃; for 48.5h; Ice-bath;	90%

: 39925-12-7
methyl 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxylate

: 36791-04-5
ribavirin

Conditions

Conditions	Yield
With ammonia In methanol overnight;	91.3%
With ammonia In methanol at 20℃; for 24h;	80%

Raw Materials

53-84-9

65-46-3

118-00-3

Downstream Products

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History

Ribavirin (36791-04-5) is a synthetic chemical not natural. It was first synthesized in 1970 (Lau, 2002—see hepcassoc.org external link below) at ICN Pharmaceuticals, Inc. (later Valeant Pharmaceuticals International) by chemist Joseph T. Witkowski, under the direction of laboratory director Roland K. Robins. This was inspired in part by discovery (in the 1960s) of antiviral activity from naturally-occurring purine-like nucleoside antibiotics like showdomycin, coformycin, and pyrazomycin. These agents had too much toxicity to be clinically useful (and the antiviral activity of them may be incidental), but they served as the starting point for pharmaceutical chemists interested in antivirals and antimetabolic chemotherapeutic agents.
In 1972 it was reported that ribavirin was active against a variety of RNA and DNA viruses in culture and in animals, without undue toxicity.Some results repoted in human trials against experimental influenza infection were mixed, however, and the FDA ultimately did not approve this indication for ribavirin use in humans, thereby causing a severe financial shock to ICN.
Though ICN was allowed in 1980 to market ribavirin,it is in inhalant form for RSV infection in children.By the time oral ribavirin was finally approved by the FDA as part of a combination treatment (with interferon) for hepatitis C in 1998, the original ICN patents on ribavirin itself had expired, and (notwithstanding subsequent patent disputes) ribavirin had become essentially a generic drug.

Specification

Ribavirin is an anti-viral drug indicated for severe RSV infection (individually), hepatitis C infection, and other viral infections. With the CAS NO. 36791-04-5, Ribavirin is Merck Sharp & Dohme Corp.'s brand name for ribavirin, a synthetic nucleoside analogue (purine analogue). The chemical name of ribavirin is 1-β-D-ribofuranosyl-1H-1,2,4-triazole-3-carboxamide. Ribavirin is a white, crystalline powder. It is freely soluble in water and slightly soluble in anhydrous alcohol. The empirical formula is C₈H₁₂N₄O₅ and the molecular weight is 244.21.

Physical properties about Ribavirin are: (1)ACD/LogP: -1.85; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -1.85; (4)ACD/LogD (pH 7.4): -1.85; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 2.35; (8)ACD/KOC (pH 7.4): 2.35; (9)#H bond acceptors: 9; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 6; (12)Index of Refraction: 1.823; (13)Molar Refractivity: 51.088 cm³; (14)Molar Volume: 117.055 cm³; (15)Polarizability: 20.253 10-24cm³; (16)Surface Tension: 106.78099822998 dyne/cm; (17)Density: 2.086 g/cm³; (18)Flash Point: 340.728 °C; (19)Enthalpy of Vaporization: 99.283 kJ/mol; (20)Boiling Point: 639.782 °C at 760 mmHg

Uses of Ribavirin: Ribavirin is used as broad-spectrum nucleoside antiviral medicine. Ribavirin is active against a number of DNA and RNA viruses. It is a member of the nucleoside antimetabolite drugs that interfere with duplication of viral genetic material. In the U.K. and the U.S. the oral (capsule or tablet) form of ribavirin is used in the treatment of hepatitis C, in combination with pegylated interferon drugs.

When you are using this chemical, please be cautious about it as the following:
1. Avoid exposure - obtain special instruction before use;
2. Do not breathe dust;
3. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
4. Wear suitable gloves and eye/face protection;
5. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C8H12N4O5/c9-6(16)7-10-2-12(11-7)8-5(15)4(14)3(1-13)17-8/h2-5,8,13-15H,1H2,(H2,9,16)/t3-,4-,5-,8-/m1/s1;
(2)InChIKey=IWUCXVSUMQZMFG-AFCXAGJDSA-N;
(3)Smilesn1([C@@H]2O[C@H](CO)[C@H]([C@H]2O)O)nc(C(N)=O)nc1

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LDLo	unreported	1500mg/kg (1500mg/kg)	KIDNEY, URETER, AND BLADDER: OTHER CHANGES GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BLOOD: HEMORRHAGE	Pharmaceutical Chemistry Journal Vol. 18, Pg. 667, 1984.
mouse	LD50	intraperitoneal	1300mg/kg (1300mg/kg)		Journal of Medicinal Chemistry. Vol. 15, Pg. 1150, 1972.
mouse	LDLo	oral	4gm/kg (4000mg/kg)		Pharmaceutical Chemistry Journal Vol. 18, Pg. 667, 1984.
rat	LD50	oral	2700mg/kg (2700mg/kg)		Pharmaceutical Chemistry Journal Vol. 18, Pg. 667, 1984.

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