Details of the Drug

General Information of Drug (ID: DMXJ7O8)

• Drug Name: Vitamin C
• Synonyms: l-ascorbic acid; vitamin C; 50-81-7; L(+)-Ascorbic acid; Ascorbicap; Cevitamic acid; Ascoltin; Hybrin; Secorbate; Proscorbin; Lemascorb; Ascorteal; Ascorbajen; Vitascorbol; Vitamisin; Natrascorb; Citriscorb; Cescorbat; Ascorbutina; Testascorbic; Cevitamin; Cetemican; Allercorb; Vitacimin; Roscorbic; Laroscorbine; Viscorin; Redoxon; Cenetone; Cegiolan; Cebicure; Ascorvit; Viforcit; Concemin; Cevital; Cergona; Cemagyl; Cebione; Cantaxin; Ascorin; Vitacee; Vicelat; Cevimin; Cetamid; Cenolate; Celaskon; Vitacin; Adenex; Ascorb; Ascorbicab; Ascorbicin; Ascorbinsaeure; Cantan; Cebid; Cebion; Cecon; Ceglion; Celin; Cemill; Cereon; Cetebe; Cevalin; Cevatine; Cevex; Cevibid; Cevitan; Cevitex; Cewin; Ciamin; Cipca; Colascor; Cortalex; Duoscorb; Ferancee; Hicee; Magnorbin; Ribena; Scorbacid; Semidehydroascorbate; Sodascorbate; Stuartinic; Sunkist; Tolfrinic; Vitace; Xitix; Acid Ascorbic; Acide ascorbique; Acido ascorbico; Acidum ascorbicum; Acidum ascorbinicum; Antiscorbic vita min; Antiscorbic vitamin; Antiscorbutic factor; Antiscorbutic vitamin; Ascorbyl radical; Catavin C; Ce lent; Component of Cortalex; Component of Endoglobin Forte; Component of Ferancee; Davitamon C; Ferrous ascorbate; Kyselina askorbova; Kyselina askorbova [Czech]; Magnesium Ascorbicum; Monodehydroascorbic acid; Natrascorb injectable; Oral Vitamin C; Planavit C; Roscorbi c; Vicomin C; Acide ascorbique [INN-French]; Acido ascorbico [INN-Spanish]; Acidum ascorbicum [INN-Latin]; Arco-cee; Ascoltin (TN); Ascorbic Acid, Monosodium Salt; Ascorbicap (TN); C-Level; C-Long; C-Quin; C-Span; C-Vimin; Cee-Caps TD; Cee-Vite; Cee-caps td; Cetane-Caps TC; Cetane-Caps TD; Cevi-Bid; Component of E and C-Level; IDO-C; Iron(II) ascorbate; Iron-ascorbic acid complexes; L-Ascorbic acid; L-Lyxoascorbic acid; L-Xyloascorbic acid; L-ascorbic acid; Liqui-Cee; Meri-C; Sodium Ascorbate (Ascorbic Acid); Vitamin-C; Ascorbic acid [BAN:INN:JAN]; Ascorbic acid [INN:BAN:JAN]; CE-VI-Sol; Ce-Mi-Lin; Dora-C-500; L-3-Ketothreohexuronic acid lactone; L-3-ketothreohexuronic acid; L-Ascorbic acid, free radical form; Ascor-bid; Ascorbic acid (JP15/USP/INN); Ascor-BID; L-(+)-Ascorbic Acid; L-threo-Hex-2-enonic acid, gamma-lactone; L-threo-hex-1-eofuranos-3-ulose; L-threo-hex-2-enono-1,4-lactone; (2R)-2-[(1S)-1,2-Dihydroxyethyl]-4,5-dihydroxy-furan-3-one; (2R)-2-[(1S)-1,2-dihydroxyethyl]-4,5-dihydroxyfuran-3-one; (5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one; 2-(1,2-Dihydroxyethyl)-4,5-dihydroxyfuran-3-one; 3-Keto-L-gulofuranolactone; 3-Oxo-L-gulofuranolactone; 3-Oxo-L-gulofuranolactone (enol form); [14C]ascorbic acid

Indication

Disease Entry	ICD 11	Status	REF
Adenocarcinoma	2D40	Approved	[1]
Carcinoma	2A00-2F9Z	Approved	[2]
Coagulation defect	3B10.0	Approved	[3]
Desmoplastic small round cell tumor	N.A.	Approved	[4]
Plasma cell myeloma	2A83.1	Approved	[5]
Refractory plasma cell neoplasm	N.A.	Approved	[6]
Shock	MG40	Approved	[7]
Vitamin C deficiency	5B56	Approved	[8]
Vitamin deficiency	5B55-5B71	Approved	[9]
Urinary tract infection	GC08	Phase 2	[8]

• Therapeutic Class: Vitamins
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 176.12
  Logarithm of the Partition Coefficient (xlogp); -1.6
  Rotatable Bond Count (rotbonds); 2
  Hydrogen Bond Donor Count (hbonddonor); 4
  Hydrogen Bond Acceptor Count (hbondacc); 6
• ADMET Property:
  Absorption: The absorption of drug is 70% to 90% []
  Bioavailability: 99% of drug becomes completely available to its intended biological destination(s) [10]
  Clearance: The drug present in the plasma can be removed from the body at the rate of 1.05 mL/min/kg [11]
  Elimination: 25% of drug is excreted from urine in the unchanged form [12]
  Half-life: The concentration or amount of drug in body reduced by one-half in 16 days [11]
  Metabolism: The drug is metabolized via the hepatic []
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 567.77191 micromolar/kg/day [13]
  Unbound Fraction: The unbound fraction of drug in plasma is 0.26% [11]
  Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.35 L/kg [11]
  Water Solubility: The ability of drug to dissolve in water is measured as 333 mg/mL [12]
• Chemical Identifiers:
  Formula: C6H8O6
  IUPAC Name: (2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one
  Canonical SMILES: C([C@@H]([C@@H]1C(=C(C(=O)O1)O)O)O)O
  InChI: InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1
  InChIKey: CIWBSHSKHKDKBQ-JLAZNSOCSA-N
• Cross-matching ID:
  PubChem CID: 54670067
  ChEBI ID: CHEBI:29073
  CAS Number: 50-81-7
  DrugBank ID: DB00126
  TTD ID: D07AHW
  VARIDT ID: DR00289
  INTEDE ID: DR0144
• Repurposed Drugs (RPD): Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Collagen (CO)	TTK982E	NOUNIPROTAC	Activator	[14]
Solute carrier family 23 member 1 (SLC23A1)	TT6XAGK	S23A1_HUMAN	Modulator	[15]
Solute carrier family 23 member 2 (SLC23A2)	TTOP832	S23A2_HUMAN	Modulator	[16]

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Sodium-dependent vitamin C transporter 1 (SLC23A1)	DT3KH2X	S23A1_HUMAN	Substrate	[17]
Sodium-dependent vitamin C transporter 2 (SLC23A2)	DTVY9PJ	S23A2_HUMAN	Substrate	[18]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Thiopurine methyltransferase (TPMT)	DEFQ8VO	TPMT_HUMAN	Substrate	[19]
Prolyl 4-hydroxylase alpha-1 (P4HA1)	DESO5ZY	P4HA1_HUMAN	Substrate	[20]
Prolyl 4-hydroxylase alpha-2 (P4HA2)	DE5EGK0	P4HA2_HUMAN	Substrate	[20]
HIF-prolyl hydroxylase 2 (EGLN1)	DEWO724	EGLN1_HUMAN	Substrate	[21]
Prolyl 4-hydroxylase alpha-3 (P4HA3)	DE2L4RX	P4HA3_HUMAN	Substrate	[22]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1 (HSD3B1)	OTNAZVKB	3BHS1_HUMAN	Gene/Protein Processing	[23]
Adenylate cyclase type 6 (ADCY6)	OTFOY4WW	ADCY6_HUMAN	Gene/Protein Processing	[24]
Alanine--tRNA ligase, cytoplasmic (AARS1)	OTW8D813	SYAC_HUMAN	Gene/Protein Processing	[25]
Aldo-keto reductase family 1 member B1 (AKR1B1)	OTRX72TH	ALDR_HUMAN	Post-Translational Modifications	[26]
Aldo-keto reductase family 1 member B10 (AKR1B10)	OTOA4HTH	AK1BA_HUMAN	Gene/Protein Processing	[27]
Aldo-keto reductase family 1 member C2 (AKR1C2)	OTQ2XMO3	AK1C2_HUMAN	Gene/Protein Processing	[27]
Alkaline phosphatase, tissue-nonspecific isozyme (ALPL)	OTG7J4BP	PPBT_HUMAN	Gene/Protein Processing	[28]
Amyloid-beta precursor protein (APP)	OTKFD7R4	A4_HUMAN	Biotransformations	[29]
Apolipoprotein A-I (APOA1)	OT5THARI	APOA1_HUMAN	Gene/Protein Processing	[30]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[31]

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Vitamin C (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Sucralfate	DMP9HBO	Moderate	Altered absorption of Vitamin C caused by Sucralfate.	Acne vulgaris [ED80]	[32]
Ephedrine	DMMV0KW	Minor	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Vitamin C caused by Ephedrine mediated altered urine pH.	Asthma [CA23]	[33]
Lisdexamfetamine	DM6W8V5	Moderate	Decreased absorption of Vitamin C due to altered gastric pH caused by Lisdexamfetamine.	Attention deficit hyperactivity disorder [6A05]	[34]
Amphetamine	DMSZQAK	Moderate	Decreased absorption of Vitamin C due to altered gastric pH caused by Amphetamine.	Attention deficit hyperactivity disorder [6A05]	[34]
Pseudoephedrine	DMIVJ0D	Minor	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Vitamin C caused by Pseudoephedrine mediated altered urine pH.	Breathing abnormality [MD11]	[33]
Propranolol	DM79NTF	Minor	Altered absorption of Vitamin C caused by Propranolol.	Migraine [8A80]	[35]
Dextroamphetamine	DMMIHVP	Moderate	Decreased absorption of Vitamin C due to altered gastric pH caused by Dextroamphetamine.	Narcolepsy [7A20]	[34]
Benzphetamine	DMIJATC	Moderate	Decreased absorption of Vitamin C due to altered gastric pH caused by Benzphetamine.	Obesity [5B80-5B81]	[34]
Methamphetamine	DMPM4SK	Moderate	Decreased absorption of Vitamin C due to altered gastric pH caused by Methamphetamine.	Pain [MG30-MG3Z]	[36]
Mexiletine	DMCTE9R	Minor	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Vitamin C caused by Mexiletine mediated altered urine pH.	Ventricular tachyarrhythmia [BC71]	[37]
Flecainide	DMSQDLE	Minor	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Vitamin C caused by Flecainide mediated altered urine pH.	Ventricular tachyarrhythmia [BC71]	[38]

References

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• [13] Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
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• [18] Molecular characterization and transcriptional regulation of the sodium-dependent vitamin C transporter genes (slc23a1 and slc23a2) in a teleost fish, the Senegalese sole (Solea senegalensis). Comp Biochem Physiol B Biochem Mol Biol. 2012 Mar;161(3):208-18.
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• [22] Identification and characterization of a third human, rat, and mouse collagen prolyl 4-hydroxylase isoenzyme. J Biol Chem. 2003 Nov 28;278(48):47685-93.
• [23] Ascorbic acid transported by sodium-dependent vitamin C transporter 2 stimulates steroidogenesis in human choriocarcinoma cells. Endocrinology. 2008 Jan;149(1):73-83.
• [24] Ascorbic acid inhibits PMP22 expression by reducing cAMP levels. Neuromuscul Disord. 2007 Mar;17(3):248-53. doi: 10.1016/j.nmd.2006.12.008. Epub 2007 Feb 15.
• [25] Antiproliferative effect of ascorbic acid is associated with the inhibition of genes necessary to cell cycle progression. PLoS One. 2009;4(2):e4409.
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