Loratadine

Details

• Internal ID: 2eed1cd5-0272-4eb9-a634-41efc00067e3
• Taxonomy: Organoheterocyclic compounds > Benzocycloheptapyridines
• IUPAC Name: ethyl 4-(13-chloro-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene)piperidine-1-carboxylate
• SMILES (Canonical): CCOC(=O)N1CCC(=C2C3=C(CCC4=C2N=CC=C4)C=C(C=C3)Cl)CC1
• SMILES (Isomeric): CCOC(=O)N1CCC(=C2C3=C(CCC4=C2N=CC=C4)C=C(C=C3)Cl)CC1
• InChI: InChI=1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3
• InChI Key: JCCNYMKQOSZNPW-UHFFFAOYSA-N
• Popularity: 4,059 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₃ClN₂O₂
• Molecular Weight: 382.90 g/mol
• Exact Mass: 382.1448057 g/mol
• Topological Polar Surface Area (TPSA): 42.40 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.89
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 79794-75-5
• Claritin
• Alavert
• Loratidine
• Clarityn
• Lisino
• Clarityne
• Loracert
• Loradex
• Bonalerg
• Claritine
• Fristamin
• Histaloran
• Lertamine
• Lorastine
• Loratyne
• Civeran
• Loranox
• Versal
• Aerotina
• Alerpriv
• Allertidin
• Anhissen
• Claratyne
• Lorantis
• Loritine
• Lowadina
• Polaratyne
• Restamine
• Sch 29851
• Sensibit
• Biloina
• Lesidas
• Loradif
• Loraver
• Lorfast
• Nularef
• Optimin
• Sanelor
• Sohotin
• Tadine
• Velodan
• Lergy
• Pylor
• Zeos
• Sinhistan Dy
• Bedix Loratadina
• Talorat Dy
• Claritin Reditabs
• Clarinase Reperabs
• Clarinase
• Rhinase
• Rinomex
• Alarin
• Sch-29851
• Clarityne-D
• Children's Claritin
• Loratadina
• Loratadinum
• Loratadinum [Latin]
• Claratyne Cold
• Claritin reditab
• Loratadina [Spanish]
• Clarityne Dy Repetabs
• Loratadine Redidose
• Clarium
• Claratyne Decongestant
• Claritin Hives Relief
• Claritin D
• Bactimicina allergy
• Claritin Hives Relief Reditab
• HSDB 3578
• UNII-7AJO3BO7QN
• 7AJO3BO7QN
• ethyl 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate
• Loratadine-d5
• MFCD00672869
• Claritin (TN)
• Loratadine [USAN:BAN:INN]
• NSC-758628
• Topcare childrens allergy relief
• DTXSID2023224
• 1398065-63-8
• Ethyl 4-(8-chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-1-piperidinecarboxylate
• CHEMBL998
• BAY76-2211
• MLS000069647
• CHEBI:6538
• DTXCID903224
• 1-Piperidinecarboxylic acid, 4-(8-chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-, ethyl ester
• Loratadine [USAN:USP:INN:BAN]
• Loratadinum (Latin)
• NSC721075
• CLARITIN-D COMPONENT LORATADINE
• NSC 721075
• NSC 758628
• 1-Piperidinecarboxylic acid, 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-, ethyl ester
• ethyl 4-(8-chloro-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridin-11-ylidene)piperidine-1-carboxylate
• ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate
• NCGC00015619-09
• LORATADINE COMPONENT OF CLARITIN-D
• SMR000058255
• L 9664
• LORATADINE (MART.)
• LORATADINE [MART.]
• LORATADINE (USP-RS)
• LORATADINE [USP-RS]
• 4-(8-Chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-1-piperidinecarboxylic Acid Ethyl Ester
• ethyl 4-(13-chloro-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene)piperidine-1-carboxylate
• Ethyl 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate
• LORATADINE (EP IMPURITY)
• LORATADINE [EP IMPURITY]
• LORATADINE (EP MONOGRAPH)
• LORATADINE [EP MONOGRAPH]
• LORATADINE (USP MONOGRAPH)
• LORATADINE [USP MONOGRAPH]
• Roletra
• 1-piperidinecarboxylic acid,4-(8-chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-,ethyl ester
• 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cycloheptal[1,2-b]pyridin-11-ylidene-1-piperidinecarboxylic acid ethyl ester
• C22H23ClN2O2
• CAS-79794-75-5
• SR-01000075968
• Allerclear
• Cronopen
• Flonidan
• Klaritin
• Loradamed
• Sch29851
• Wal-itin
• loratadine-form1
• LoratadineI-p25
• Loratadine,(S)
• Claritine (TN)
• Clarityne (TN)
• Fristamin (TN)
• Symphoral (TN)
• Clarityn (TN)
• Flonidan (TN)
• 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylic acid ethyl ester
• Loratadine- Bio-X
• Alavert (TN)
• AllergyX (TN)
• Lomilan (TN)
• Lorfast (TN)
• Rinolan (TN)
• Roletra (TN)
• Tidilor (TN)
• loratadine-form2-He
• Loratadine Wyeth Brand
• Spectrum_001496
• Tocris-1944
• LORATADINE [MI]
• LORATADINE [INN]
• LORATADINE [JAN]
• LoratadineI-0deg(L13)
• Opera_ID_1868
• Spectrum2_001584
• Spectrum3_000740
• Spectrum4_000177
• Spectrum5_001650
• Lopac-L-9664
• LORATADINE [HSDB]
• LORATADINE [USAN]
• LoratadineI-p80(L13)
• Wyeth Brand of Loratadine
• LORATADINE [VANDF]
• D06ABF
• LoratadineI-m100(L13)
• LoratadineI-m173(L13)
• SCHEMBL4596
• Desloratadine EP Impurity C
• LORATADINE [WHO-DD]
• Lopac0_000680
• Oprea1_027965
• REGID_for_CID_3957
• BSPBio_002300
• KBioGR_000693
• KBioSS_001976
• Loratadine (JAN/USP/INN)
• MLS000758260
• MLS001148466
• MLS001423984
• Alavert, Claritin, Loratadine
• BIDD:GT0198
• DivK1c_000792
• Loratadine (JAN/USAN/INN)
• Loratadine [USAN:INN:BAN]
• SPECTRUM1503712
• SPBio_001548
• GTPL7216
• LORATADINE [ORANGE BOOK]
• BDBM22876
• HMS502H14
• KBio1_000792
• KBio2_001976
• KBio2_004544
• KBio2_007112
• KBio3_001520
• R06AX13
• NINDS_000792
• HMS2051G11
• HMS2090O18
• HMS2093I15
• HMS2235G23
• HMS3262G21
• HMS3268M16
• HMS3371D13
• HMS3393G11
• HMS3412N06
• HMS3654L17
• HMS3676N06
• HMS3714E09
• Pharmakon1600-01503712
• Loratadine 0.1 mg/ml in Methanol
• AMY15355
• BCP22338
• Tox21_110185
• Tox21_301532
• Tox21_500680
• BBL010757
• CCG-39362
• DL-436
• NSC758628
• s1358
• STK574925
• AKOS005499513
• Loratadine, >=98% (HPLC), powder
• Tox21_110185_1
• AB06849
• AC-2086
• BCP9000858
• CCG-100786
• CS-0887
• CS-O-07780
• DB00455
• KS-1079
• LP00680
• NC00036
• NSC-721075
• SDCCGSBI-0050659.P004
• IDI1_000792
• NCGC00015619-01
• NCGC00015619-02
• NCGC00015619-03
• NCGC00015619-04
• NCGC00015619-05
• NCGC00015619-06
• NCGC00015619-07
• NCGC00015619-08
• NCGC00015619-10
• NCGC00015619-11
• NCGC00015619-12
• NCGC00015619-13
• NCGC00015619-26
• NCGC00023125-02
• NCGC00023125-04
• NCGC00023125-05
• NCGC00023125-06
• NCGC00023125-07
• NCGC00255171-01
• NCGC00261365-01
• BL164637
• HY-17043
• NCI60_041473
• SY052751
• BCP0726000007
• SBI-0050659.P003
• LS-114660
• EU-0100680
• FT-0627976
• L0223
• SW197416-3
• D00364
• EN300-119520
• AB00053224-15
• AB00053224-16
• AB00053224_17
• AB00053224_18
• L000667
• Q424049
• Q-100833
• SR-01000075968-1
• SR-01000075968-3
• SR-01000075968-4
• SR-01000075968-6
• BRD-K82795137-001-02-3
• BRD-K82795137-001-10-6
• Z1521553845
• Loratadine, British Pharmacopoeia (BP) Reference Standard
• Loratadine, European Pharmacopoeia (EP) Reference Standard
• Loratadine, United States Pharmacopeia (USP) Reference Standard
• Loratadine, Pharmaceutical Secondary Standard; Certified Reference Material
• Loratadine for system suitability, European Pharmacopoeia (EP) Reference Standard
• 1-Piperidenecarboxylic acid, 4-(8-chloro-5,6-duhydro-11H-benzo [5,6]cyclohepta[1,2-b]-pyridin-11-ylidene)-, ethyl ester
• 1-Piperidenecarboxylic acid,6-duhydro-11H-benzo [5,6]cyclohepta[1,2-b]-pyridin-11-ylidene)-, ethyl ester
• 1-Piperidinecarboxylic acid,4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-, ethyl ester
• 11-[N-(ethoxycarbonyl)-4-piperidylidene]-8-chloro-6,11-dihydro-5H-benzo-[5,6]cyclohepta[1,2-b]pyridine
• 4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene-1-piperidinecarboxylic acidethyl ester
• 4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidine-1-carboxylic acid ethyl ester
• 4-(8-chloro-5,6-dihydrobenzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylic acid ethyl ester
• 8-chloro-11-(1-ethoxycarbonyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine
• 8-chloro-6,11-dihydro-11-(1- ethoxycarbonyl-4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine
• 8-Chloro-6,11-dihydro-11-(1-ethoxycarbonyl-4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine
• Ethyl 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidine)-1-piperidinecarboxylate
• ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0,3,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate
• loratadine impurity c;4-(4,8-dichloro-5,6-dihydro-11h-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-1-piperidinecarboxylic acid ethyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9969	99.69%
Caco-2	+	0.5491	54.91%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7744	77.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9139	91.39%
OATP1B3 inhibitior	+	0.9435	94.35%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9126	91.26%
P-glycoprotein inhibitior	+	0.8312	83.12%
P-glycoprotein substrate	+	0.9035	90.35%
CYP3A4 substrate	+	0.7980	79.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7948	79.48%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.9818	98.18%
CYP inhibitory promiscuity	+	0.9359	93.59%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8100	81.00%
Carcinogenicity (trinary)	Non-required	0.6408	64.08%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9823	98.23%
Skin irritation	-	0.7816	78.16%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	-	0.6637	66.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.8917	89.17%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8185	81.85%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.6237	62.37%
Acute Oral Toxicity (c)	II	0.4705	47.05%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.7267	72.67%
Glucocorticoid receptor binding	+	0.6759	67.59%
Aromatase binding	-	0.5124	51.24%
PPAR gamma	+	0.6681	66.81%
Honey bee toxicity	-	0.9344	93.44%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5189	51.89%
Fish aquatic toxicity	+	0.9905	99.05%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	25118.9 nM	Potency	via CMAUP
CHEMBL2047	Q96RI1	Bile acid receptor FXR	3070 nM	IC50	PMID: 23688559
CHEMBL1293237	P54132	Bloom syndrome protein	28183.8 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	31622.8 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	2800 nM; 16 nM	IC50; IC50	PMID: 22328583; via CMAUP
CHEMBL3721	P10632	Cytochrome P450 2C8	2950 nM	IC50	PMID: 22328583
CHEMBL3397	P11712	Cytochrome P450 2C9	39.8 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	< 100 nM	IC50	PMID: 22328583
CHEMBL340	P08684	Cytochrome P450 3A4	6309.6 nM; 6309.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293278	O75496	Geminin	31622.8 nM	Potency	via CMAUP
CHEMBL240	Q12809	HERG	169.82 nM; 173 nM; 169.82 nM; 169.82 nM; 169.82 nM; 173.78 nM; 173.78 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50	via Super-PRED; PMID: 12190308; PMID: 12873512; PMID: 15911273; PMID: 18448342; PMID: 21185626; PMID: 19110341
CHEMBL231	P35367	Histamine H1 receptor	170 nM; 290 nM	IC50; IC50	via CMAUP; PMID: 16220969
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	19952.6 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	10000 nM; 25118.9 nM; 12589.3 nM; 28183.8 nM; 35481.3 nM	Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	7943.3 nM; 12589.3 nM; 3981.1 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL4302	P08183	P-glycoprotein 1	11400 nM	IC50	PMID: 11454724
CHEMBL1293298	Q01453	Peripheral myelin protein 22	42561.5 nM	Potency	via CMAUP
CHEMBL3401	O75469	Pregnane X receptor	10000 nM; 10000 nM; 12600 nM	EC50; EC50; EC50	PMID: 20966043; PMID: 20966043; PMID: 20966043
CHEMBL1293235	P02545	Prelamin-A/C	11220.2 nM; 31622.8 nM; 15848.9 nM; 22387.2 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	23280.9 nM	Potency	via CMAUP
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	245 nM	IC50	via CMAUP
CHEMBL3351189	Q9H2J7	Sodium-dependent neutral amino acid transporter B(0)AT2	4000 nM	IC50	PMID: 25318072
CHEMBL1293232	Q16637	Survival motor neuron protein	31622.8 nM; 11220.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	19952.6 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	19952.6 nM; 39810.7 nM; 19952.6 nM; 39810.7 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	12589.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.58%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	97.40%	95.17%
CHEMBL2581	P07339	Cathepsin D	96.77%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.77%	86.33%
CHEMBL3691	Q13822	Autotaxin	94.26%	96.39%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.95%	94.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	92.90%	93.10%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	92.02%	96.00%
CHEMBL2047	Q96RI1	Bile acid receptor FXR	91.28%	96.10%
CHEMBL4208	P20618	Proteasome component C5	91.01%	90.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	89.49%	96.67%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	88.69%	90.24%
CHEMBL1951	P21397	Monoamine oxidase A	88.48%	91.49%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	87.27%	93.65%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.98%	95.78%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	86.54%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	85.51%	94.73%
CHEMBL6007	O75762	Transient receptor potential cation channel subfamily A member 1	83.74%	92.17%
CHEMBL5028	O14672	ADAM10	82.53%	97.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.07%	95.89%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.62%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.29%	96.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.13%	98.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.38%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.34%	99.17%

Plants that contains it

• Sesamum indicum

Cross-Links

• PubChem: 3957
• NPASS: NPC116961
• ChEMBL: CHEMBL998