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Histamine
Histamine
2D structure of histamine
Histamine
3D structure of histamine
Names
Synonyms 5-imidazoleethylamine, eramin, ergamine, ergotidine and theramine
Brand names Ceplene, Histatrol

IUPAC name
IUPAC name
2-(1H-imidazol-5-yl)ethanamine
Clinical information
Preg. cat.
AU: N/A
US: C
Legal status
AU: Prescription Only Medicine (S4)
CA: ℞-only
UK: POM
US: ℞-only
Routes Inhalation, ID, IV, SC

Salts Dihydrochloride, phosphate
Identifiers
ATC code L03AX14 (2HCl), V04CG03 (2H3PO4)
ChemSpider 753
DrugBank
2H3PO4 2HCl


DB00667 DB05381


PubChem 774
MedlinePlus None
MeSH ID D006632
PDB IDs
PDBs
1AVN (RCSB, PDBe; X-ray)
1NP1 (RCSB, PDBe; X-ray)
1QFT (RCSB, PDBe; X-ray)
1QFV (RCSB, PDBe; X-ray)
1IKE (RCSB, PDBe; X-ray)
1KAR (RCSB, PDBe; X-ray)
1JQD (RCSB, PDBe; X-ray)
1U18 (RCSB, PDBe; X-ray)
2QEB (RCSB, PDBe; X-ray)
2X45 (RCSB, PDBe; X-ray)
3BU1 (RCSB, PDBe; X-ray)
3G7X (RCSB, PDBe; X-ray)
3RXH (RCSB, PDBe; X-ray)
External links
DailyMed histamine-phosphate search
Drugs.com international, monograph
Jmol 3D structure
Licensing data EU EMA: link.
US FDA: link.
MSR N/A
emc histamine search
TGA-eBS histamine search
Chemical properties
Formula C5H9N3
Mol. mass
Mol. mass for MFs
111.1451 g/mol
SMILES
SMILES
C1=C(NC=N1)CCN
InChI
InChI
1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)
InChIKey
InChIKey
NTYJJOPFIAHURM-UHFFFAOYSA-N


Histidine

L-histidine

Histamine, a chemical signalling molecule that has diverse roles in the CNS and the periphery. It is biosynthesized from the amino acid L-histidine.[1]

CNS rolesEdit

In the CNS it acts via the H1 and H3 receptors, H1 is excitatory while H3 is an inhibitory auto- and hetero- receptor.[1] H1 receptor activation improves wakefulness, whereas blocking this receptor is responsible for the sedating effect of many drugs, especially the first antihistamines to be developed.[1]

Peripheral rolesEdit

In the periphery it acts via H1, H2 and H4 receptors. H1 receptors play a crucial role in mediating allergic responses in the body, it is via blocking this receptor that the family of drugs, the antihistamines, achieve their anti-allergy effects.[1] H2 receptors, on the other hand, is secreted by the cells of the stomach in order to induce the release of stomach acid.[1] Consequently H2 antagonists produce inhibitory effects on the release of stomach acid and are used to treat stomach ulcers and related conditions.[1] H4 receptors are expressed primarily in immune cells and appears to play a role in immune responses, similarly to the H1 receptor.[1]

Medical use of histamineEdit

Exogenous histamine, that is histamine that comes from sources other than the body produces smooth muscle stimulation, leading to bronchoconstriction (that is, the airways close up) and reduced blood pressure (due to dilation of the blood vessels).[2] When it comes into contact with the skin it leads to a hypersensitivity reaction similar to allergic reactions (including red dots of skin that are raised and swollen and discomfort; usually used as a test for leprosy-induced nerve damage).[2] In the European Union it is also approved for use, in combination with a low-dose of aldesleukin, as post-consolidation therapy (to prevent future relapse) in people with acute myeloid leukaemia.[3][4][5]


External linksEdit

Reference listEdit

  1. 1.0 1.1 1.2 1.3 1.4 1.5 1.6 Walter, M; Stark, H (January 2012). "Histamine receptor subtypes: a century of rational drug design.". Frontiers in Bioscience 4: 461–88. PMID 22202071. 
  2. 2.0 2.1 Brayfield, A, ed. (30 January 2013). "Histamine". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 13 September 2014. 
  3. "Ceplene : EPAR - Product Information". European Medicines Agency. Solna, Sweden: Meda AB. 10 April 2014. Retrieved 5 December 2014. 
  4. Yang, LP; Perry, CM (1 January 2011). "Histamine dihydrochloride: in the management of acute myeloid leukaemia.". Drugs 71 (1): 109–22. PMID 21175244. doi:10.2165/11206410-000000000-00000. 
  5. Schlenk, RF (November 2014). "Post-remission therapy for acute myeloid leukemia.". Haematologica 99 (11): 1663–1670. PMC 4222459. PMID 25420282. doi:10.3324/haematol.2014.114611. 
Antineoplastic and immunomodulating agents (ATC:L)
Antineoplastic agents (L01)
(A)
N. mustards
(AA)
OZPPs Cyclophosphamide, ifosfamide, trofosfamide
PhDs Bendamustine, chlorambucil, melphalan, prednimustine
Other Chlormethine
Alkyl sulfonates
(AB)
Busulfan, mannosulfan, treosulfan
Ethylene imines
(AC)
Carboquone, thiotepa, triaziquone
Nitrosoureas
(AD)
Acyclical Carmustine, ranimustine
Cyclical Fotemustine, lomustine, semustine
Sugars Nimustine, streptozocin
Methylating-As
(AX, XB01)
Dacarbazine, procarbazine, temozolomide
Epoxides
(AG, AX)
Etoglucid, mitobronitol
Others
(AX, XX)
Altretamine, pipobroman
Antimetabolites
(B)
Folic acid-As
(BA)
DHFR-Is Aminopterin, methotrexate, pemetrexed, pralatrexate
TS-Is Pemetrexed, raltitrexed
Purine-As
(BB)
ADA-I Penostatin
RNR-Is Cladribine, clofarabine, fludarabine
G-Ds Mercaptopurine, tioguanine
Pyrimidine-As (BC) DMT-Is Azacitidine, decitabine
DPM-I Cytarabine, enocitabine
RNR-I Gemcitabine
TS-Is Capecitabine, carmofur, floxuridine, fluorouracil, tegafur
Others
(XX05)
RNR-I Hydroxycarbamide
Natural products
(C)
Vinca alkaloids (CA) Vinblastine, vincristine, vindesine, vinflunine, vinorelbine, vintafolide
Podophyllotoxins (CB) Etoposide, teniposide
Colchicine-D
(CC)
Demecolcine
Taxanes
(CD)
Cabazitaxel, docetaxel, paclitaxel, paclitaxel poliglumex
Camptothecins (XX) Irinotecan, topotecan
Other
(CX, XX)
Omacetaxine mepesuccinate, trabectedin
(D) Actinomycines (DA) Dactinomycin
Anthraquinones
(DB)
Cyclines Aclarubicin, amrubicin, daunorubicin, doxorubicin, epirubicin, idarubicin, pirarubicin, pixantrone, sabarubicin, valrubicin, zorubicin
CDs Mitoxantrone, pixantrone
Others
(DC)
Bleomycin, ixabepilone, mitomycin, peplomycin, plicamycin, zinostatin
Others
(X)
Pt compounds
(XA)
Carboplatin, cisplatin, eptaplatin, nedaplatin, oxaliplatin, picoplatin, polyplatillen, satraplatin
Monoclonal antibodies
(-mab)
(XC)
Chimeric
(-tuxi-)
Cetuximab, brentuximab vedotin, rituximab, siltuximab
Human
(-mu-, others)
Ipilimumab, nivolumab, ofatumumab, panitumumab, ramucirumab
Humanized
(-zu-)
Alemtuzumab, bevacizumab, gemtuzumab, mogamulizumab, nimotuzumab, obinutuzumab, pertuzumab, trastuzumab, trastuzumab emtansine
Murine
(-mo-, -axo-[n 1])
Catumaxomab, ibritumomab, tositumomab
PK inhibitors
(XE)
BRAF
(-rafenib)
Dabrafenib, vemurafenib
mTOR
(-rolimus)
Everolimus, ridaforolimus, temsirolimus
TK
(-nib)
Afatinib, axitinib, bosutinib, crizotinib, dasatinib, erlotinib, gefitinib, ibrutinib, imatinib, lapatinib, masitinib, nilotinib, pazopanib, ponatinib, regorafenib, ruxolitinib, sorafenib, sunitinib, trametinib, vandetanib
Others
(XX)
HDAC-Is Panobinostat, romidepsin, vorinostat
Microtubule Is Eribulin, estramustine
Oligo-/poly-mers Oblimersen, sizofiran
Proteasome Is
(-zomib)
Bortezomib, carfilzomib
Proteins Aflibercept, asparaginase, denileukin diftitox, endostatin, pegaspargase
Retinoids Alitretinoin, bexarotene, tamibarotene, tretinoin
TII Is Amsacrine, sobuzoxane
M enzyme Is Aceglatone, anagrelide, ubenimex
Others Arsenic trioxide, celecoxib, lonidamine, masoprocol, miltefosine, mitoguazone, mitotane, sitimagene ceradenovec
Endocrine therapy (L02)
Hormones and RAs
(A)
Oestrogens
(AA)
Diethylstilbestrol, ethinylestradiol, fosfestrol, polyestradiol phosphate
Progestogens
(AB)
Medroxyprogesterone, megestrol, gestonorone
GnRH analogues
(AE)
Buserelin, goserelin, histrelin, leuprorelin, triptorelin
Hormones antagonists and RAs
(B)
Anti-oestrogens
(BA)
Fulvestrant, tamoxifen, toremifene
Anti-androgens
(BB)
Bicalutamide, flutamide, nilutamide
Aromatase inhibitors
(BG)
Aminoglutethimide, anastrozole, exemestane, formestane, letrozole, vorozole
Others
(BX)
Abarelix, abiraterone, degarelix.
Immunostimulants (L03, L03A)
Colony-stimulating factors (CSFs)
(A)
G- Filgrastim (lipegfilgrastim, pegfilgrastim), lenograstim
GM- Molgramostim, sargramostim
Others Ancestim, mirimostim, thrombopoietin
Interferons (IFNs)
(B)
Alfa Interferon alfa-2a (peginterferon alfa-2a, peginterferon alfa-2a combinations), interferon alfa-2b (albinterferon alfa-2b, peginterferon alfa-2b, peginterferon alfa-2a combinations), interferon alfacon-1, interferon alfa-n1, interferon alfa natural
Beta Interferon beta-1a, interferon beta-1b, interferon beta natural
Gamma Interferon gamma
Interleukins (ILs)
(C)
Aldesleukin (IL-2), oprelvekin (IL-11)
Others
(AX)
Endogenous Histamine dihydrochloride, pegademase, tasonermin, thymopentin
Vaccines/
antigens
BCG vaccines, melanoma vaccine, mifamurtide, sipuleucel-T, vitespen
Polymers Lentinan, Poly I:C, Poly ICLC
Others Cridanimod, glatiramer acetate, pidotimod, plerixafor, roquinimex
Immunosuppressants (L04, L04A)
Selective agents
(A)
Antibodies Human mAbs Belimumab
Humanized mAbs Eculizumab, efalizumab, natalizumab
Murine mAbs Muromonab-CD3
Polyclonal Antithymocyte immunoglobulin
FPs Abatacept, alefacept, belatacept
mTOR inhibitors
(-rolimus)
Everolimus, sirolimus
IL-2 inhibitors
(-imus)
Abetimus, gusperimus
AMs Leflunomide, mycophenolic acid, teriflunomide
Others Apremilast, fingolimod, tofacitinib
TNF-α inhibitors
(B)
FPs Etanercept
mAbs Adalimumab, afelimomab, certolizumab pegol, golimumab, infliximab.
Interleukin inhibitors
(C)
IL-1 Anakinra, canakinumab, rilonacept
IL-2 Basiliximab, daclizumab
IL-5 Mepolizumab
IL-6 Siltuximab, tocilizumab, ustekinumab
IL-12 Briakinumab, ustekinumab
IL-17A Secukinumab
Calcineurin inhibitors
(D)
Cyclophilin-B
(-closporin)
Ciclosporin, voclosporin
FKBP12-binding
(-crolimus)
Pimecrolimus, tacrolimus
Others
(X)
Antimetabolites Azathioprine, fludarabine, mercaptopurine, methotrexate
IMiDs Lenalidomide, pomalidomide, thalidomide
Others Cyclophosphamide, mitoxantrone, pirfenidone
  1. Murine/rat hybrids

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