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Showing drug card for Citalopram (DB00215)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:06:34
Primary Accession Number DB00215
Secondary Accession Number
  • APRD00147
Name Citalopram
Drug Type
  • Approved
  • Small Molecule
Description A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from tardive dyskinesia in preference to tricyclic antidepressants, which aggravate this condition. [PubChem]
Synonyms
  1. Citalopram Hydrobromide
  2. Citalopramum [INN-Latin]
Brand Names
  1. Celexa
  2. Cipram
  3. Nitalapram
Brand Mixtures Not Available
Chemical IUPAC Name 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile
Chemical Formula C20H21FN2O
Chemical Structure Structure
CAS Registry Number 59729-33-8
InChI Identifier InChI=1/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3
InChI Key WSEQXVZVJXJVFP-UHFFFAOYAV
KEGG Drug Not Available
KEGG Compound C07572 Link Image
PubChem Compound 2771 Link Image
PubChem Substance 183529 Link Image
ChEBI ID 3723 Link Image
PharmGKB ID PA449015 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02248051 Link Image
RxList Link http://www.rxlist.com/cgi/generic/citalo.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Citalopram Link Image
FDA Label
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference K. P. Boegesoe, A. S. Toft, U.S. Pat. 4,136,193 (1979)
Average Molecular Weight 324.3919
Monoisotopic Molecular Weight 324.1638
State Solid
Melting Point 182-183oC
Experimental Water Solubility 31 mg/L Source: PhysProp
Predicted Water Solubility 5.88e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 3.5 Source: PhysProp
Predicted LogP 3.58 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.74 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CN(C)CCC[C@@]1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
Canonical SMILES CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
Drug Category
  • Antidepressants
  • Antidepressive Agents, Second-Generation
  • Selective Serotonin Reuptake Inhibitors (SSRIs)
  • Serotonin Uptake Inhibitors
ATC Codes
AHFS Codes
  • 28:16.04.20
Indication For the treatment of depression.
Pharmacology Citalopram is one of a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs). It is used to treat the depression associated with mood disorders. It is also used on occassion in the treatment of body dysmorphic disorder and anxiety. The antidepressant, antiobsessive-compulsive, and antibulimic actions of Citalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. In vitro studies show that Citalopram is a potent and selective inhibitor of neuronal serotonin reuptake and has only very weak effects on norepinephrine and dopamine neuronal reuptake. Citalopram has no significant affinity for adrenergic (alpha1, alpha2, beta), cholinergic, GABA, dopaminergic, histaminergic, serotonergic (5HT1A, 5HT1B, 5HT2), or benzodiazepine receptors; antagonism of such receptors has been hypothesized to be associated with various anticholinergic, sedative, and cardiovascular effects for other psychotropic drugs. The chronic administration of Citalopram was found to downregulate brain norepinephrine receptors, as has been observed with other drugs effective in the treatment of major depressive disorder. Citalopram does not inhibit monoamine oxidase.
Mechanism of Action The antidepressant, antiobsessive-compulsive, and antibulimic actions of Citalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. Citalopram blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT1A autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.
Absorption Bioavailability is 80% following oral administration.
Toxicity Symptoms most often accompanying citalopram overdose, alone or in combination with other drugs and/or alcohol, included dizziness, sweating, nausea, vomiting, tremor, somnolence, and sinus tachycardia. In more rare cases, observed symptoms included amnesia, confusion, coma, convulsions, hyperventilation, cyanosis, rhabdomyolysis, and ECG changes (including QTc prolongation, nodal rhythm, ventricular arrhythmia, and very rare cases of torsade de pointes). Acute renal failure has been very rarely reported accompanying overdose.
Protein Binding 50%
Biotransformation Hepatic.
Half Life 35 hours
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acenocoumarol The SSRI increases the effect of anticoagulant
Almotriptan Increased risk of CNS adverse effects
Anisindione The SSRI increases the effect of anticoagulant
Carvedilol The SSRI increases the effect of the beta-blocker
Clarithromycin Possible serotoninergic syndrome with this combination
Clozapine The antidepressant increases the effect of clozapine
Dicumarol The SSRI increases the effect of anticoagulant
Eletriptan Increased risk of CNS adverse effects
Erythromycin Possible serotoninergic syndrome with this combination
Frovatriptan Increased risk of CNS adverse effects
Isocarboxazid Possible severe adverse reaction with this combination
Josamycin Possible serotoninergic sydrome with this combination
Linezolid Combination associated with possible serotoninergic syndrome
Metoprolol The SSRI increases the effect of the beta-blocker
Moclobemide Possible serotoninergic syndrome
Naratriptan Increased risk of CNS adverse effects
Oxycodone Increased risk of serotonin syndrome
Phenelzine Possible severe adverse reaction with this combination
Pimozide This SSRI increases the effect and toxicity of pimozide
Propranolol This SSRI increases the effect of the beta-blocker
Rasagiline Possible severe adverse reaction with this combination
Rizatriptan Increased risk of CNS adverse effects
Selegiline Possible severe adverse reaction with this combination
Sibutramine Risk of serotoninergic syndrome
St. John's Wort St. John's Wort increases the effect and toxicity of the SSRI
Sumatriptan Increased risk of CNS adverse effects
Tramadol Increased risk of serotonin syndrome
Tranylcypromine Possible severe adverse reaction with this combination
Troleandomycin Possible serotoninergic syndrome with this combination
Warfarin The SSRI increases the effect of anticoagulant
Zolmitriptan Increased risk of CNS adverse effects
Food Interactions
  • Avoid St.John's Wort.
  • Avoid alcohol.
  • Take without regard to meals.
Pathways Not Available
General References
  1. Atmaca M, Kuloglu M, Tezcan E, Semercioz A: The efficacy of citalopram in the treatment of premature ejaculation: a placebo-controlled study. Int J Impot Res. 2002 Dec;14(6):502-5. [PubMed Link Image]
  2. Sindrup SH, Bjerre U, Dejgaard A, Brosen K, Aaes-Jorgensen T, Gram LF: The selective serotonin reuptake inhibitor citalopram relieves the symptoms of diabetic neuropathy. Clin Pharmacol Ther. 1992 Nov;52(5):547-52. [PubMed Link Image]
  3. Clayton A, Keller A, McGarvey EL: Burden of phase-specific sexual dysfunction with SSRIs. J Affect Disord. 2006 Mar;91(1):27-32. Epub 2006 Jan 20. [PubMed Link Image]
  4. Andersen G, Vestergaard K, Riis JO: Citalopram for post-stroke pathological crying. Lancet. 1993 Oct 2;342(8875):837-9. [PubMed Link Image]
  5. Drugs.com Link Image
  6. Wikipedia Link Image
  7. RxList Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 2C19 (CYP2C19)
  2. Cytochrome P450 2D6 (CYP2D6)
  3. Monoamine oxidase type B (MAO-B)
Targets
  1. Sodium-dependent serotonin transporter
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 2C19 (CYP2C19)
Enzyme 1 Gene Name CYP2C19
Enzyme 1 SwissProt ID P33261 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P33261|CP2CJ_HUMAN Cytochrome P450 2C19 (EC 1.14.13.80) 
MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDVSKSLTNLSKI
YGPVFTLYFGLERMVVLHGYEVVKEALIDLGEEFSGRGHFPLAERANRGFGIVFSNGKRW
KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS
IIFQKRFDYKDQQFLNLMEKLNENIRIVSTPWIQICNNFPTIIDYFPGTHNKLLKNLAFM
ESDILEKVKEHQESMDINNPRDFIDCFLIKMEKEKQNQQSEFTIENLVITAADLLGAGTE
TTSTTLRYALLLLLKHPEVTAKVQEEIERVVGRNRSPCMQDRGHMPYTDAVVHEVQRYID
LIPTSLPHAVTCDVKFRNYLIPKGTTILTSLTSVLHDNKEFPNPEMFDPRHFLDEGGNFK
KSNYFMPFSAGKRICVGEGLARMELFLFLTFILQNFNLKSLIDPKDLDTTPVVNGFASVP
PFYQLCFIPV
Phase 1 Metabolizing Enzyme 2 [top]
Enzyme 2 Name Cytochrome P450 2D6 (CYP2D6)
Enzyme 2 Gene Name CYP2D6
Enzyme 2 SwissProt ID P10635 Link Image
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 Protein Sequence >sp|P10635|CP2D6_HUMAN Cytochrome P450 2D6 (EC 1.14.14.1) 
MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVDFQNTPYCFDQ
LRRRFGDVFSLQLAWTPVVVLNGLAAVREALVTHGEDTADRPPVPITQILGFGPRSQGVF
LARYGPAWREQRRFSVSTLRNLGLGKKSLEQWVTEEAACLCAAFANHSGRPFRPNGLLDK
AVSNVIASLTCGRRFEYDDPRFLRLLDLAQEGLKEESGFLREVLNAVPVLLHIPALAGKV
LRFQKAFLTQLDELLTEHRMTWDPAQPPRDLTEAFLAEMEKAKGNPESSFNDENLRIVVA
DLFSAGMVTTSTTLAWGLLLMILHPDVQRRVQQEIDDVIGQVRRPEMGDQAHMPYTTAVI
HEVQRFGDIVPLGMTHMTSRDIEVQGFRIPKGTTLITNLSSVLKDEAVWEKPFRFHPEHF
LDAQGHFVKPEAFLPFSAGRRACLGEPLARMELFLFFTSLLQHFSFSVPTGQPRPSHHGV
FAFLVSPSPYELCAVPR
Phase 1 Metabolizing Enzyme 3 [top]
Enzyme 3 Name Monoamine oxidase type B (MAO-B)
Enzyme 3 Gene Name MAOB
Enzyme 3 SwissProt ID P27338 Link Image
Enzyme 3 SNPs SNPJam Report Link Image
Enzyme 3 Protein Sequence >sp|P27338|AOFB_HUMAN Amine oxidase B 
SNKCDVVVVGGGISGMAAAKLLHDSGLNVVVLEARDRVGGRTYTLRNQKVKYVDLGGSYV
GPTQNRILRLAKELGLETYKVNEVERLIHHVKGKSYPFRGPFPPVWNPITYLDHNNFWRT
MDDMGREIPSDAPWKAPLAEEWDNMTMKELLDKLCWTESAKQLATLFVNLCVTAETHEVS
ALWFLWYVKQCGGTTRIISTTNGGQERKFVGGSGQVSERIMDLLGDRVKLERPVIYIDQT
RENVLVETLNHEMYEAKYVISAIPPTLGMKIHFNPPLPMMRNQMITRVPLGSVIKCIVYY
KEPFWRKKDYCGTMIIDGEEAPVAYTLDDTKPEGNYAAIMGFILAHKARKLARLTKEERL
KKLCELYAKVLGSLEALEPVHYEEKNWCEEQYSGGCYTTYFPPGILTQYGRVLRQPVDRI
YFAGTETATHWSGYMEGAVEAGERAAREILHAMGKIPEDEIWQSEPESVDVPAQPITTTF
LERHLPSVPGLLRLIGLTTIFSATALGFLAHKRGLLVRV
Drug Target 1 [top]
Target 1 ID 824
Target 1 Name Sodium-dependent serotonin transporter
Target 1 Synonyms
  1. 5HT transporter
  2. 5HTT
Target 1 Gene Name SLC6A4
Target 1 Protein Sequence >Sodium-dependent serotonin transporter 
METTPLNSQKQLSACEDGEDCQENGVLQKVVPTPGDKVESGQISNGYSAVPSPGAGDDTR
HSIPATTTTLVAELHQGERETWGKKVDFLLSVIGYAVDLGNVWRFPYICYQNGGGAFLLP
YTIMAIFGGIPLFYMELALGQYHRNGCISIWRKICPIFKGIGYAICIIAFYIASYYNTIM
AWALYYLISSFTDQLPWTSCKNSWNTGNCTNYFSEDNITWTLHSTSPAEEFYTRHVLQIH
RSKGLQDLGGISWQLALCIMLIFTVIYFSIWKGVKTSGKVVWVTATFPYIILSVLLVRGA
TLPGAWRGVLFYLKPNWQKLLETGVWIDAAAQIFFSLGPGFGVLLAFASYNKFNNNCYQD
ALVTSVVNCMTSFVSGFVIFTVLGYMAEMRNEDVSEVAKDAGPSLLFITYAEAIANMPAS
TFFAIIFFLMLITLGLDSTFAGLEGVITAVLDEFPHVWAKRRERFVLAVVITCFFGSLVT
LTFGGAYVVKLLEEYATGPAVLTVALIEAVAVSWFYGITQFCRDVKEMLGFSPGWFWRIC
WVAISPLFLLFIICSFLMSPPQLRLFQYNYPYWSIILGYCIGTSSFICIPTYIAYRLIIT
PGTFKERIIKSITPETPTEIPCGDIRLNAV
Target 1 Number of Residues 640
Target 1 Molecular Weight 70325
Target 1 Theoretical pI 6.17
Target 1 GO Classification
Function
transporter activity
neurotransmitter transporter activity
neurotransmitter:sodium symporter activity
Process
physiological process
cellular physiological process
transport
neurotransmitter transport
Component
cell
membrane
intrinsic to membrane
integral to membrane
integral to plasma membrane
Target 1 General Function Involved in serotonin:sodium symporter activity
Target 1 Specific Function Terminates the action of serotonine by its high affinity sodium-dependent reuptake into presynaptic terminals
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 88-108
  • 116-135
  • 160-180
  • 253-271
  • 280-297
  • 333-350
  • 362-383
  • 417-436
  • 464-482
  • 498-518
  • 539-558
  • 577-595
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 36433 Link Image
Target 1 UniProtKB/Swiss-Prot ID P31645 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name SC6A4_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1893 bp 
ATGGAGACGACGCCCTTGAATTCTCAGAAGCAGCTATCAGCGTGTGAAGATGGAGAAGAT
TGTCAGGAAAACGGAGTTCTACAGAAGGTTGTTCCCACCCCAGGGGACAAAGTGGAGTCC
GGGCAAATATCCAATGGGTACTCAGCAGTTCCAAGTCCTGGTGCGGGAGATGACACACGG
CACTCTATCCCAGCGACCACCACCACCCTAGTGGCTGAGCTTCATCAAGGGGAACGGGAG
ACCTGGGGCAAGAAGGTGGATTTCCTTCTCTCAGTGATTGGCTATGCTGTGGACCTGGGC
AATGTCTGGCGCTTCCCCTACATATGTTACCAGAATGGAGGGGGGGCATTCCTCCTCCCC
TACACCATCATGGCCATTTTTGGGGGAATCCCGCTCTTTTACATGGAGCTCGCACTGGGA
CAGTACCACCGAAATGGATGCATTTCAATATGGAGGAAAATCTGCCCGATTTTCAAAGGG
ATTGGTTATGCCATCTGCATCATTGCCTTTTACATTGCTTCCTACTACAACACCATCATG
GCCTGGGCGCTATACTACCTCATCTCCTCCTTCACGGACCAGCTGCCCTGGACCAGCTGC
AAGAACTCCTGGAACACTGGCAACTGCACCAATTACTTCTCCGAGGACAACATCACCTGG
ACCCTCCATTCCACGTCCCCTGCTGAAGAATTTTACACGCGCCACGTCCTGCAGATCCAC
CGGTCTAAGGGGCTCCAGGACCTGGGGGGCATCAGCTGGCAGCTGGCCCTCTGCATCATG
CTGATCTTCACTGTTATCTACTTCAGCATCTGGAAAGGCGTCAAGACCTCTGGCAAGGTG
GTGTGGGTGACAGCCACCTTCCCTTATATCATCCTTTCTGTCCTGCTGGTGAGGGGTGCC
ACCCTCCCTGGAGCCTGGAGGGGTGTTCTCTTCTACTTGAAACCCAATTGGCAGAAACTC
CTGGAGACAGGGGTGTGGATAGATGCAGCCGCTCAGATCTTCTTCTCTCTTGGTCCGGGC
TTTGGGGTCCTGCTGGCTTTTGCTAGCTACAACAAGTTCAACAACAACTGCTACCAAGAT
GCCCTGGTGACCAGCGTGGTGAACTGCATGACGAGCTTCGTTTCGGGATTTGTCATCTTC
ACAGTGCTCGGTTACATGGCTGAGATGAGGAATGAAGATGTGTCTGAGGTGGCCAAAGAC
GCAGGTCCCAGCCTCCTCTTCATCACGTATGCAGAAGCGATAGCCAACATGCCAGCGTCC
ACTTTCTTTGCCATCATCTTCTTTCTGATGTTAATCACGCTGGGCTTGGACAGCACGTTT
GCAGGCTTGGAGGGGGTGATCACGGCTGTGCTGGATGAGTTCCCACACGTCTGGGCCAAG
CGCCGGGAGCGGTTCGTGCTCGCCGTGGTCATCACCTGCTTCTTTGGATCCCTGGTCACC
CTGACTTTTGGAGGGGCCTACGTGGTGAAGCTGCTGGAGGAGTATGCCACGGGGCCCGCA
GTGCTCACTGTCGCGCTGATCGAAGCAGTCGCTGTGTCTTGGTTCTATGGCATCACTCAG
TTCTGCAGGGACGTGAAGGAAATGCTCGGCTTCAGCCCGGGGTGGTTCTGGAGGATCTGC
TGGGTGGCCATCAGCCCTCTGTTTCTCCTGTTCATCATTTGCAGTTTTCTGATGAGCCCG
CCACAACTACGACTTTTCCAATATAATTATCCTTACTGGAGTATCATCTTGGGTTACTGC
ATAGGAACCTCATCTTTCATTTGCATCCCCACATATATAGCTTATCGGTTGATCATCACT
CCAGGGACATTTAAAGAGCGTATTATTAAAAGTATTACCCCGGAGACACCAACAGAAATT
CCTTGTGGGGACATCCGCTTGAATGCTGTGTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID SLC6A4 Link Image
Target 1 GenAtlas ID SLC6A4 Link Image
Target 1 HGNC ID HGNC:11050 Link Image
Target 1 Chromosome Location 17
Target 1 Locus 17q11.1-q12
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Cargill M, Altshuler D, Ireland J, Sklar P, Ardlie K, Patil N, Shaw N, Lane CR, Lim EP, Kalyanaraman N, Nemesh J, Ziaugra L, Friedland L, Rolfe A, Warrington J, Lipshutz R, Daley GQ, Lander ES: Characterization of single-nucleotide polymorphisms in coding regions of human genes. Nat Genet. 1999 Jul;22(3):231-8. [PubMed Link Image]
  2. Caspi A, Sugden K, Moffitt TE, Taylor A, Craig IW, Harrington H, McClay J, Mill J, Martin J, Braithwaite A, Poulton R: Influence of life stress on depression: moderation by a polymorphism in the 5-HTT gene. Science. 2003 Jul 18;301(5631):386-9. [PubMed Link Image]
  3. Ramamoorthy S, Bauman AL, Moore KR, Han H, Yang-Feng T, Chang AS, Ganapathy V, Blakely RD: Antidepressant- and cocaine-sensitive human serotonin transporter: molecular cloning, expression, and chromosomal localization. Proc Natl Acad Sci U S A. 1993 Mar 15;90(6):2542-6. [PubMed Link Image]
  4. Lesch KP, Wolozin BL, Murphy DL, Reiderer P: Primary structure of the human platelet serotonin uptake site: identity with the brain serotonin transporter. J Neurochem. 1993 Jun;60(6):2319-22. [PubMed Link Image]
  5. Lesch KP, Wolozin BL, Estler HC, Murphy DL, Riederer P: Isolation of a cDNA encoding the human brain serotonin transporter. J Neural Transm Gen Sect. 1993;91(1):67-72. [PubMed Link Image]
Target 1 Drug References
  1. Eriksson E, Engberg G, Bing O, Nissbrandt H: Effects of mCPP on the extracellular concentrations of serotonin and dopamine in rat brain. Neuropsychopharmacology. 1999 Mar;20(3):287-96. [PubMed Link Image]
  2. Maines LW, Keck BJ, Smith JE, Lakoski JM: Corticosterone regulation of serotonin transporter and 5-HT1A receptor expression in the aging brain. Synapse. 1999 Apr;32(1):58-66. [PubMed Link Image]
  3. Vicentic A, Battaglia G, Carroll FI, Kuhar MJ: Serotonin transporter production and degradation rates: studies with RTI-76. Brain Res. 1999 Sep 11;841(1-2):1-10. [PubMed Link Image]
  4. Dugar A, Keck BJ, Maines LW, Miller S, Njai R, Lakoski JM: Compensatory responses in the aging hippocampal serotonergic system following neurodegenerative injury with 5,7-dihydroxytryptamine. Synapse. 2001 Feb;39(2):109-21. [PubMed Link Image]
  5. Dutta AK, Fei XS, Beardsley PM, Newman JL, Reith ME: Structure-activity relationship studies of 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine derivatives and their N-analogues: evaluation of O-and N-analogues and their binding to monoamine transporters. J Med Chem. 2001 Mar 15;44(6):937-48. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.