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Tox | Related Drugs | BioActivity |

Stem definition	Drug id	CAS RN
arabinofuranosyl derivatives	1892	121032-29-9

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: nelarabine arranon nelzarabine atriance	prodrug of ara-G Molecular weight: 297.27 Formula: C11H15N5O5 CLOGP: -0.39 LIPINSKI: 0 HAC: 10 HDO: 4 TPSA: 148.77 ALOGS: -1.33 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

nelarabine
arranon
nelzarabine
atriance

prodrug of ara-G

Molecular weight: 297.27
Formula: C11H15N5O5
CLOGP: -0.39
LIPINSKI: 0
HAC: 10
HDO: 4
TPSA: 148.77
ALOGS: -1.33
ROTB: 3

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

None

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	2.97 mg/mL	Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine)	6.60 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	4.23 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	11 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	4.90 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	81 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.80 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	0.50 hours	Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Property	Description	Value	Unit	Confidence	Similarity
azlogd74	LogD at pH 7.4	-0.474		High	1
caco2-efflux	Caco-2 efflux ratio (BA/AB)	29.785		High	1
caco2-intrinsic-papp	Caco-2 intrinsic apparent permeability	1.016	10^-6 cm/s	High	1
dh-clint	Dog hepatocyte intrinsic clearance	1.183	uL/min/10^6 cells	High	1
dppb	Dog plasma protein binding (% unbound)	79.210	%	High	1
fcs-ppb	Fetal calf serum protein binding (% unbound)	86.720	%	High	1
herg	hERG pIC50	3.793	pIC50	High	1
hh-clint	Human hepatocyte intrinsic clearance	1.288	uL/min/10^6 cells	High	1
hlm-clint	Human liver microsomal intrinsic clearance	3.327	uL/min/mg protein	High	1
hppb	Human plasma protein binding (% unbound)	69.660	%	High	1
mdck-mdr1-efflux	MDCK-MDR1 efflux ratio	3.639		High	1
mh-clint	Mouse hepatocyte intrinsic clearance	1.439		High	1
mppb	Mouse plasma protein binding (% unbound)	89.270		High	1
nih-mdck-mdr1-efflux	NIH MDCK-MDR1 efflux ratio	2.203		High	1
pfas-class	PFAS structural alert (1 = True, 0 = False)	0
pppb	Pig plasma protein binding (% unbound)	86.800	%	High	1
rh-clint	Rat hepatocyte intrinsic clearance	2.023	uL/min/10^6 cells	High	1
rh-fuinc	Rat hepatocyte fraction unbound in incubation	93.450	%	High	1
rppb	Rat plasma protein binding (% unbound)	85.310	%	High	1
solubility-dd	Solubility at pH 7.4 in DMSO	895.365	uM	High	1

Approvals:

Date	Agency	Company	Orphan
Oct. 28, 2005	FDA	NOVARTIS PHARMS CORP
Aug. 22, 2007	EMA	Sandoz Pharmaceuticals d.d.

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Myelopathy	127.93	63.70	22	625	3422	90624378
Subacute combined cord degeneration	94.31	63.70	12	635	229	90627571
Peripheral sensory neuropathy	77.65	63.70	17	630	9233	90618567

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Myelopathy	122.95	42.92	28	1876	2863	42616568
Guillain-Barre syndrome	79.76	42.92	24	1880	7239	42612192
Fibrinous bronchitis	72.31	42.92	11	1893	116	42619315
Scedosporium infection	60.38	42.92	14	1890	1544	42617887
Neurotoxicity	58.50	42.92	26	1878	23625	42595806
Neuropathy peripheral	56.27	42.92	42	1862	101811	42517620
Febrile neutropenia	56.01	42.92	54	1850	185649	42433782
Leukoencephalopathy	48.52	42.92	15	1889	4939	42614492
Stenotrophomonas infection	48.35	42.92	14	1890	3690	42615741
Peripheral sensory neuropathy	47.57	42.92	17	1887	8745	42610686
Ataxia	47.29	42.92	20	1884	16105	42603326

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Myelopathy	243.53	43.67	49	2464	5527	110581259
Peripheral sensory neuropathy	137.76	43.67	38	2475	16642	110570144
Neurotoxicity	129.53	43.67	45	2468	42162	110544624
Guillain-Barre syndrome	129.37	43.67	33	2480	10711	110576075
Febrile neutropenia	101.85	43.67	72	2441	316695	110270091
Subacute combined cord degeneration	89.97	43.67	14	2499	354	110586432
Fibrinous bronchitis	77.47	43.67	11	2502	145	110586641
Neuropathy peripheral	77.35	43.67	49	2464	179228	110407558
Peripheral motor neuropathy	76.97	43.67	18	2495	4068	110582718
Scedosporium infection	63.43	43.67	14	2499	2444	110584342
Hypertriglyceridaemia	60.40	43.67	20	2493	16134	110570652
Muscular weakness	58.59	43.67	47	2466	248421	110338365
Polyneuropathy	57.26	43.67	23	2490	31989	110554797
Stenotrophomonas infection	51.35	43.67	14	2499	5844	110580942
Sensory loss	51.15	43.67	19	2494	21438	110565348
Pseudomonal bacteraemia	50.50	43.67	13	2500	4358	110582428
Ataxia	48.26	43.67	20	2493	30088	110556698

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	L01BB07	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS ANTIMETABOLITES Purine analogues
FDA MoA	N0000000233	Nucleic Acid Synthesis Inhibitors
FDA EPC	N0000175595	Nucleoside Metabolic Inhibitor
CHEBI has role	CHEBI:35610	antineoplastic agent
CHEBI has role	CHEBI:50266	prodrug
CHEBI has role	CHEBI:59517	DNA synthesis inhibitor

Related Drugs by ATC class:

L01BB Purine analogues 5 drugs

cladribine clofarabine fludarabine phosphate mercaptopurine thioguanine

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
T-cell acute lymphoblastic leukemia	indication	277575008
Precursor T-cell lymphoblastic lymphoma	indication	421246008
Hyperbilirubinemia	contraindication	14783006	DOID:2741
Peripheral demyelinating neuropathy	contraindication	23414001	DOID:5214
Demyelination	contraindication	32693004
Dehydration	contraindication	34095006
Mental handicap	contraindication	47437004
Hepatic failure	contraindication	59927004
Seizure disorder	contraindication	128613002
Intrathecal injection of chemotherapeutic agent	contraindication	171765004
Impaired renal function disorder	contraindication	197663003
Anemia	contraindication	271737000	DOID:2355
Drowsy	contraindication	271782001
Pregnancy, function	contraindication	289908002
Thrombocytopenic disorder	contraindication	302215000	DOID:1588
Peripheral nerve disease	contraindication	302226006
Neutropenic disorder	contraindication	303011007	DOID:1227
Breastfeeding (mother)	contraindication	413712001
Radiation Therapy of Cranium	contraindication
Severe Leukopenia	contraindication
Radiation Therapy of Vertebral Column	contraindication
Chemotherapy-Induced Hyperuricemia	contraindication

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	11.67	acidic
pKa2	12.33	acidic
pKa3	13.34	acidic
pKa4	3.39	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

None

External reference:

ID	Source
4025093	VUID
N0000175345	NUI
D05134	KEGG_DRUG
4025093	VANDF
C0907349	UMLSCUI
CHEMBL1201112	ChEMBL_ID
DB01280	DRUGBANK_ID
C104457	MESH_SUPPLEMENTAL_RECORD_UI
3011155	PUBCHEM_CID
7090	IUPHAR_LIGAND_ID
7704	INN_ID
60158CV180	UNII
274771	RXNORM
20608	MMSL
354214	MMSL
72483	MMSL
d05655	MMSL
011068	NDDF
418538001	SNOMEDCT_US
418784008	SNOMEDCT_US
C0050203	UMLSCUI
CHEBI:63612	CHEBI
38819-10-2	SECONDARY_CAS_RN
135499520	PUBCHEM_CID
0Z99WX0GPF	UNII

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Arranon	HUMAN PRESCRIPTION DRUG LABEL	1	0078-0683	INJECTION	5 mg	INTRAVENOUS	NDA	30 sections
Nelarabine	HUMAN PRESCRIPTION DRUG LABEL	1	14789-114	INJECTION	5 mg	INTRAVENOUS	ANDA	28 sections
Nelarabine	HUMAN PRESCRIPTION DRUG LABEL	1	25021-259	INJECTION, SOLUTION	5 mg	INTRAVENOUS	ANDA	31 sections
Nelarabine	HUMAN PRESCRIPTION DRUG LABEL	1	39822-0650	INJECTION	5 mg	INTRAVENOUS	ANDA	32 sections
Nelarabine	HUMAN PRESCRIPTION DRUG LABEL	1	43598-142	INJECTION	5 mg	INTRAVENOUS	ANDA	28 sections
NELARABINE	Human Prescription Drug Label	1	46708-813	INJECTION	5 mg	INTRAVENOUS	ANDA	27 sections
NELARABINE	Human Prescription Drug Label	1	62332-813	INJECTION	5 mg	INTRAVENOUS	ANDA	26 sections
Arranon	HUMAN PRESCRIPTION DRUG LABEL	1	66758-165	INJECTION	5 mg	INTRAVENOUS	NDA	30 sections
Nelarabine	Human Prescription Drug Label	1	68083-233	INJECTION	5 mg	INTRAVENOUS	ANDA	27 sections
Nelarabine	HUMAN PRESCRIPTION DRUG LABEL	1	70121-1743	INJECTION	5 mg	INTRAVENOUS	ANDA	28 sections
Nelarabine	HUMAN PRESCRIPTION DRUG LABEL	1	70710-1726	INJECTION	5 mg	INTRAVENOUS	ANDA	26 sections
Nelarabine	HUMAN PRESCRIPTION DRUG LABEL	1	70710-1839	INJECTION	5 mg	INTRAVENOUS	ANDA	26 sections
Nelarabine	HUMAN PRESCRIPTION DRUG LABEL	1	70771-1685	INJECTION	5 mg	INTRAVENOUS	ANDA	1 sections
Nelarabine	HUMAN PRESCRIPTION DRUG LABEL	1	71288-165	INJECTION	5 mg	INTRAVENOUS	ANDA	28 sections
Nelarabine	HUMAN PRESCRIPTION DRUG LABEL	1	71288-165	INJECTION	5 mg	INTRAVENOUS	ANDA	28 sections
NELARABINE	Human Prescription Drug Label	1	72205-154	INJECTION	5 mg	INTRAVENOUS	ANDA	25 sections
nelarabine	HUMAN PRESCRIPTION DRUG LABEL	1	81927-111	INJECTION	5 mg	INTRAVENOUS	ANDA	29 sections
nelarabine	HUMAN PRESCRIPTION DRUG LABEL	1	81927-375	INJECTION	5 mg	INTRAVENOUS	ANDA	29 sections