Template:Infobox drug/testcases-warning

Brincidofovir
Clinical data
Trade names	Tembexa
Other names	CMX001; Cidofovir-HDP; hexadecyloxypropyl-cidofovir
License data	US DailyMed: Brincidofovir;
Routes of; administration	By mouth
ATC code	J05AB17 (WHO) ;
Legal status
Legal status	US: ℞-only;
Identifiers
	IUPAC name ({[(2S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)[3-(hexadecyloxy)propoxy]phosphinic acid;
CAS Number	444805-28-1 ; Sodium salt: 496765-79-8 ;
PubChem CID	483477;
DrugBank	DB12151; Sodium salt: DBSALT002145;
ChemSpider	424003; Sodium salt: 21259112;
UNII	6794O900AX; Sodium salt: 8UN8SA9Z5C ;
KEGG	D10547;
ChEMBL	ChEMBL203321;
Chemical and physical data
Formula	C27H52N3O7P
Molar mass	561.701 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCCCCCCCCCCCOCCCOP(=O)(O)CO[C@H](CO)Cn1ccc(N)nc1=O;
	InChI InChI=1S/C27H52N3O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-35-20-16-21-37-38(33,34)24-36-25(23-31)22-30-18-17-26(28)29-27(30)32/h17-18,25,31H,2-16,19-24H2,1H3,(H,33,34)(H2,28,29,32)/t25-/m0/s1; Key:WXJFKKQWPMNTIM-VWLOTQADSA-N;

Paracetamol
Clinical data
Pronunciation	Paracetamol: /ˌpærəˈsiːtəmɒl/; Acetaminophen: /əˌsiːtəˈmɪnəfɪn/ ⓘ
Trade names	Tylenol, Panadol, others
Other names	N-acetyl-para-aminophenol (APAP), acetaminophen (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a681004
License data	US DailyMed: Acetaminophen; US FDA: Acetaminophen;
Pregnancy; category	AU: A; ;
Routes of; administration	Oral (by mouth), rectal, intravenous (IV)
Drug class	Analgesics and antipyretics
ATC code	N02BE01 (WHO) N02BE51 (WHO) N02BE71 (WHO);
Legal status
Legal status	AU: S4 (Rx), OTC, and unscheduled; CA: OTC / Rx-only; UK: General sales list (GSL, OTC); US: OTC / Rx-only;
Pharmacokinetic data
Bioavailability	63–89%
Protein binding	negligible to 10–25% in overdose
Metabolism	Predominantly in the liver
Metabolites	APAP gluc, APAP sulfate, APAP GSH, APAP cys, AM404, NAPQI
Onset of action	Pain relief onset by route:; oral – 37 minutes; Intravenous – 8 minutes
Elimination half-life	1.9–2.5 hours
Excretion	Urine
Identifiers
	IUPAC name N-(4-hydroxyphenyl)acetamide;
CAS Number	103-90-2 ;
PubChem CID	1983;
PubChem SID	46506142;
IUPHAR/BPS	5239;
DrugBank	DB00316 ;
ChemSpider	1906 ;
UNII	362O9ITL9D;
KEGG	D00217 ; C06804;
ChEBI	CHEBI:46195 ;
ChEMBL	ChEMBL112 ;
PDB ligand	TYL (PDBe, RCSB PDB);
Chemical and physical data
Formula	C8H9NO2
Molar mass	151.165 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.263 g/cm3
Melting point	169 °C (336 °F)
Solubility in water	7.21 g/kg (0 °C); 8.21 g/kg (5 °C); 9.44 g/kg (10 °C); 10.97 g/kg (15 °C); 12.78 g/kg (20 °C); ~14 mg/ml (20 °C);
	SMILES CC(=O)Nc1ccc(O)cc1;
	InChI InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10) ; Key:RZVAJINKPMORJF-UHFFFAOYSA-N ;
	(verify)

Paracetamol
Clinical data
Pronunciation	Paracetamol: /ˌpærəˈsiːtəmɒl/; Acetaminophen: /əˌsiːtəˈmɪnəfɪn/ ⓘ
Trade names	Tylenol, Panadol, others
Other names	N-acetyl-para-aminophenol (APAP), acetaminophen (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a681004
License data	US DailyMed: Acetaminophen; US FDA: Acetaminophen;
Pregnancy; category	AU: A; ;
Routes of; administration	Oral (by mouth), rectal, intravenous (IV)
Drug class	Analgesics and antipyretics
ATC code	N02BE01 (WHO) N02BE51 (WHO) N02BE71 (WHO);
Legal status
Legal status	AU: S4 (Rx), OTC, and unscheduled; CA: OTC / Rx-only; UK: General sales list (GSL, OTC); US: OTC / Rx-only;
Pharmacokinetic data
Bioavailability	63–89%
Protein binding	negligible to 10–25% in overdose
Metabolism	Predominantly in the liver
Metabolites	APAP gluc, APAP sulfate, APAP GSH, APAP cys, AM404, NAPQI
Onset of action	Pain relief onset by route:; oral – 37 minutes; Intravenous – 8 minutes
Elimination half-life	1.9–2.5 hours
Excretion	Urine
Identifiers
	IUPAC name N-(4-hydroxyphenyl)acetamide;
CAS Number	103-90-2 ;
PubChem CID	1983;
PubChem SID	46506142;
IUPHAR/BPS	5239;
DrugBank	DB00316 ;
ChemSpider	1906 ;
UNII	362O9ITL9D;
KEGG	D00217 ; C06804;
ChEBI	CHEBI:46195 ;
ChEMBL	ChEMBL112 ;
PDB ligand	TYL (PDBe, RCSB PDB);
Chemical and physical data
Formula	C8H9NO2
Molar mass	151.165 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.263 g/cm3
Melting point	169 °C (336 °F)
Solubility in water	7.21 g/kg (0 °C); 8.21 g/kg (5 °C); 9.44 g/kg (10 °C); 10.97 g/kg (15 °C); 12.78 g/kg (20 °C); ~14 mg/ml (20 °C);
	SMILES CC(=O)Nc1ccc(O)cc1;
	InChI InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10) ; Key:RZVAJINKPMORJF-UHFFFAOYSA-N ;
	(verify)

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Paracetamol

Side by side comparison

References

^ International Drug Names
^ "Acetaminophen Use During Pregnancy". Drugs.com. 14 June 2019. Archived from the original on 9 March 2020. Retrieved 25 February 2020.
^ "Regulatory Decision Summary – Acetaminophen Injection". Health Canada. 23 October 2014. Archived from the original on 7 June 2022. Retrieved 7 June 2022.
^ Working Group of the Australian and New Zealand College of Anaesthetists and Faculty of Pain Medicine (2015). Schug SA, Palmer GM, Scott DA, Halliwell R, Trinca J (eds.). Acute Pain Management: Scientific Evidence (4th ed.). Melbourne: Australian and New Zealand College of Anaesthetists (ANZCA), Faculty of Pain Medicine (FPM). ISBN 978-0-9873236-7-5. Archived from the original (PDF) on 31 July 2019. Retrieved 28 October 2019.
^ ^a ^b ^c Forrest JA, Clements JA, Prescott LF (1982). "Clinical pharmacokinetics of paracetamol". Clin Pharmacokinet. 7 (2): 93–107. doi:10.2165/00003088-198207020-00001. PMID 7039926. S2CID 20946160.
^ "Codapane Forte Paracetamol and codeine phosphate product information" (PDF). TGA eBusiness Services. Alphapharm Pty Limited. 29 April 2013. Archived from the original on 6 February 2016. Retrieved 10 May 2014.
^ "Acetaminophen Pathway (therapeutic doses), Pharmacokinetics". Archived from the original on 4 March 2016. Retrieved 13 January 2016.
^ ^a ^b Pickering G, Macian N, Libert F, Cardot JM, Coissard S, Perovitch P, Maury M, Dubray C (September 2014). "Buccal acetaminophen provides fast analgesia: two randomized clinical trials in healthy volunteers". Drug Design, Development and Therapy. 8: 1621–1627. doi:10.2147/DDDT.S63476. PMC 4189711. PMID 25302017. In postoperative conditions for acute pain of mild to moderate intensity, the quickest reported time to onset of analgesia with APAP is 8 minutes9 for the iv route and 37 minutes6 for the oral route.
^ Karthikeyan M, Glen RC, Bender A (2005). "General Melting Point Prediction Based on a Diverse Compound Data Set and Artificial Neural Networks". Journal of Chemical Information and Modeling. 45 (3): 581–590. doi:10.1021/ci0500132. PMID 15921448.
^ "melting point data for paracetamol". Lxsrv7.oru.edu. Archived from the original on 30 June 2012. Retrieved 19 March 2011.
^ ^a ^b ^c ^d ^e Granberg RA, Rasmuson AC (1999). "Solubility of paracetamol in pure solvents". Journal of Chemical & Engineering Data. 44 (6): 1391–95. doi:10.1021/je990124v.

Brincidofovir

Side by side comparison

Brincidofovir
Clinical data

Trade names	Tembexa
Other names	CMX001; Cidofovir-HDP; hexadecyloxypropyl-cidofovir
License data	US DailyMed: Brincidofovir
Routes of administration	By mouth
ATC code	J05AB17 (WHO)
Legal status
Legal status	US: ℞-only^[1]
Identifiers
IUPAC name ({[(2S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)[3-(hexadecyloxy)propoxy]phosphinic acid
CAS Number	444805-28-1^Y Sodium salt: 496765-79-8^Y
PubChem CID	483477
DrugBank	DB12151 Sodium salt: DBSALT002145
ChemSpider	424003 Sodium salt: 21259112
UNII	6794O900AX Sodium salt: 8UN8SA9Z5C^Y
KEGG	D10547
ChEMBL	ChEMBL203321
Chemical and physical data
Formula	C₂₇H₅₂N₃O₇P
Molar mass	561.701 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCCCCCCCCCCCCOCCCOP(=O)(O)CO[C@H](CO)Cn1ccc(N)nc1=O
InChI InChI=1S/C27H52N3O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-35-20-16-21-37-38(33,34)24-36-25(23-31)22-30-18-17-26(28)29-27(30)32/h17-18,25,31H,2-16,19-24H2,1H3,(H,33,34)(H2,28,29,32)/t25-/m0/s1 Key:WXJFKKQWPMNTIM-VWLOTQADSA-N

References

^ "FDA approves drug to treat smallpox". U.S. Food and Drug Administration (FDA). 4 June 2021. Archived from the original on 8 June 2021. Retrieved 7 June 2021. This article incorporates text from this source, which is in the public domain.

Albendazole

Side by side comparison

Albendazole
Clinical data


Trade names	Albenza, Valbazen, Zentel, others
AHFS/Drugs.com	Monograph
MedlinePlus	a610019
License data	US DailyMed: Albendazole
Pregnancy category	AU: D
Routes of administration	By mouth
ATC code	P02CA03 (WHO) QP52AC11 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only (for humans; veterinary suspension and paste are both OTC)^[1]
Pharmacokinetic data
Bioavailability	<5%^[2]
Protein binding	70%^[2]
Metabolism	Hepatic^[2]
Elimination half-life	8-12 hours^[2]
Excretion	Bile (humans) Urine (ruminants)
Identifiers
IUPAC name Methyl [5-(propylthio)-1H-benzoimidazol-2-yl]carbamate
CAS Number	54965-21-8^Y
PubChem CID	2082
DrugBank	DB00518^Y
ChemSpider	1998^Y
UNII	F4216019LN
KEGG	D00134^Y
ChEBI	CHEBI:16664^Y
ChEMBL	ChEMBL1483^Y
NIAID ChemDB	007895
Chemical and physical data
Formula	C₁₂H₁₅N₃O₂S
Molar mass	265.33 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	208 to 210 °C (406 to 410 °F)
SMILES CCCSc2ccc1nc(NC(=O)OC)[nH]c1c2
InChI InChI=1S/C12H15N3O2S/c1-3-6-18-8-4-5-9-10(7-8)14-11(13-9)15-12(16)17-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)^Y Key:HXHWSAZORRCQMX-UHFFFAOYSA-N^Y
(verify)

Albendazole
Clinical data


Trade names	Albenza, Valbazen, Zentel, others
AHFS/Drugs.com	Monograph
MedlinePlus	a610019
License data	US DailyMed: Albendazole
Pregnancy category	AU: D
Routes of administration	By mouth
ATC code	P02CA03 (WHO) QP52AC11 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only (for humans; veterinary suspension and paste are both OTC)^[1]
Pharmacokinetic data
Bioavailability	<5%^[2]
Protein binding	70%^[2]
Metabolism	Hepatic^[2]
Elimination half-life	8-12 hours^[2]
Excretion	Bile (humans) Urine (ruminants)
Identifiers
IUPAC name Methyl [5-(propylthio)-1H-benzoimidazol-2-yl]carbamate
CAS Number	54965-21-8^Y
PubChem CID	2082
DrugBank	DB00518^Y
ChemSpider	1998^Y
UNII	F4216019LN
KEGG	D00134^Y
ChEBI	CHEBI:16664^Y
ChEMBL	ChEMBL1483^Y
NIAID ChemDB	007895
Chemical and physical data
Formula	C₁₂H₁₅N₃O₂S
Molar mass	265.33 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	208 to 210 °C (406 to 410 °F)
SMILES CCCSc2ccc1nc(NC(=O)OC)[nH]c1c2
InChI InChI=1S/C12H15N3O2S/c1-3-6-18-8-4-5-9-10(7-8)14-11(13-9)15-12(16)17-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)^Y Key:HXHWSAZORRCQMX-UHFFFAOYSA-N^Y
(verify)

References

^ Plumb DC (2011). "Albendazole". Plumb's Veterinary Drug Handbook (7th ed.). Stockholm, Wisconsin; Ames, Iowa: Wiley. pp. 19–21. ISBN 978-0-470-95964-0.
^ ^a ^b ^c ^d "Albenza, (albendazole) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on March 1, 2014. Retrieved February 25, 2014.

[drugs.com-internatl-1] International Drug Names

[Drugs.com_pregnancy-2] "Acetaminophen Use During Pregnancy". Drugs.com. 14 June 2019. Archived from the original on 9 March 2020. Retrieved 25 February 2020.

[3] "Regulatory Decision Summary – Acetaminophen Injection". Health Canada. 23 October 2014. Archived from the original on 7 June 2022. Retrieved 7 June 2022.

[4] Working Group of the Australian and New Zealand College of Anaesthetists and Faculty of Pain Medicine (2015). Schug SA, Palmer GM, Scott DA, Halliwell R, Trinca J (eds.). Acute Pain Management: Scientific Evidence (4th ed.). Melbourne: Australian and New Zealand College of Anaesthetists (ANZCA), Faculty of Pain Medicine (FPM). ISBN 978-0-9873236-7-5. Archived from the original (PDF) on 31 July 2019. Retrieved 28 October 2019.

[pmid7039926-5] Forrest JA, Clements JA, Prescott LF (1982). "Clinical pharmacokinetics of paracetamol". Clin Pharmacokinet. 7 (2): 93–107. doi:10.2165/00003088-198207020-00001. PMID 7039926. S2CID 20946160.

[TGA-6] "Codapane Forte Paracetamol and codeine phosphate product information" (PDF). TGA eBusiness Services. Alphapharm Pty Limited. 29 April 2013. Archived from the original on 6 February 2016. Retrieved 10 May 2014.

[7] "Acetaminophen Pathway (therapeutic doses), Pharmacokinetics". Archived from the original on 4 March 2016. Retrieved 13 January 2016.

[Buccal_route-8] Pickering G, Macian N, Libert F, Cardot JM, Coissard S, Perovitch P, Maury M, Dubray C (September 2014). "Buccal acetaminophen provides fast analgesia: two randomized clinical trials in healthy volunteers". Drug Design, Development and Therapy. 8: 1621–1627. doi:10.2147/DDDT.S63476. PMC 4189711. PMID 25302017. In postoperative conditions for acute pain of mild to moderate intensity, the quickest reported time to onset of analgesia with APAP is 8 minutes9 for the iv route and 37 minutes6 for the oral route.

[9] Karthikeyan M, Glen RC, Bender A (2005). "General Melting Point Prediction Based on a Diverse Compound Data Set and Artificial Neural Networks". Journal of Chemical Information and Modeling. 45 (3): 581–590. doi:10.1021/ci0500132. PMID 15921448.

[10] "melting point data for paracetamol". Lxsrv7.oru.edu. Archived from the original on 30 June 2012. Retrieved 19 March 2011.

[paracetamol-solubility-11] Granberg RA, Rasmuson AC (1999). "Solubility of paracetamol in pure solvents". Journal of Chemical & Engineering Data. 44 (6): 1391–95. doi:10.1021/je990124v.

[FDA_Tembexa-12] "FDA approves drug to treat smallpox". U.S. Food and Drug Administration (FDA). 4 June 2021. Archived from the original on 8 June 2021. Retrieved 7 June 2021. This article incorporates text from this source, which is in the public domain.

[plumb-13] Plumb DC (2011). "Albendazole". Plumb's Veterinary Drug Handbook (7th ed.). Stockholm, Wisconsin; Ames, Iowa: Wiley. pp. 19–21. ISBN 978-0-470-95964-0.

[MSR-14] "Albenza, (albendazole) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on March 1, 2014. Retrieved February 25, 2014.

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